supportinginformation diastereoselective synthesis of vicinal · p1 11.70 usec pl1 4.00 db sfo1...

10
S1 Supporting Information Diastereoselective Synthesis of Vicinal cisDihydroxyheterospirocycles by OnePot Epoxidation/Spirocyclization of (C)3Functionalized Cyclohex2en1ols MingChang P. Yeh,* a ChiaJung Liang, a ChengYuan Liu, a Yafon Shih, a IChen Lee, a HsiangFang Liu, a JengLong Wang* b a Department of Chemistry, National Taiwan Normal University, 88 DingJou Road, Section 4, Taipei 11677, Taiwan, Republic of China Fax: (+886)229324249 email: [email protected]. b Department of Nursing, Meiho University, 23, Pingguang Rd., Neipu, Pintung, Taiwan, Republic of China Fax: (+886)915686889 email: [email protected] Contents of Supporting Information Copies of all 1 H and 13 C NMR Spectra of Compounds 16, 1823 and 2829. S2 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2013

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Page 1: SupportingInformation Diastereoselective Synthesis of Vicinal · P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 Processing parameters SI 16384 ... Date_ 20120712 Time 21.57 INSTRUM

S1

Supporting Information

Diastereoselective Synthesis of Vicinal cis-­Dihydroxyheterospirocycles by One-­Pot Epoxidation/Spirocyclization of (C)-­3-­Functionalized

Cyclohex-­2-­en-­1-­ols

Ming-­Chang P. Yeh,*a Chia-­Jung Liang,

a Cheng-­Yuan Liu,

a Ya-­fon Shih,

a I-­Chen

Lee,a Hsiang-­Fang Liu,

a Jeng-­Long Wang*

b

a Department of Chemistry, National Taiwan Normal University, 88 Ding-­Jou Road,

Section 4, Taipei 11677, Taiwan, Republic of China

Fax: (+886)-­2-­29324249;; e-­mail: [email protected].

b Department of Nursing, Meiho University, 23, Pingguang Rd., Neipu, Pintung,

Taiwan, Republic of China

Fax: (+886)-­915686889;; e-­mail: [email protected]

Contents of Supporting Information Copies of all

1H and

13C NMR Spectra of Compounds 16, 18–23 and 28–29. S2

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 2: SupportingInformation Diastereoselective Synthesis of Vicinal · P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 Processing parameters SI 16384 ... Date_ 20120712 Time 21.57 INSTRUM

S2

10 9 8 7 6 5 4 3 2 1 0 ppm

1.643

1.656

1.664

1.682

1.690

1.698

1.706

1.718

1.730

1.752

1.797

1.810

1.833

1.843

1.860

1.966

1.978

1.992

1.995

2.002

2.013

2.030

2.523

2.540

2.549

2.556

2.565

2.588

2.596

2.607

2.612

2.624

2.638

3.731

3.739

4.059

4.071

4.080

4.088

5.790

1.262

1.180

3.181

1.014

1.000

Current Data ParametersNAME amy20120808EXPNO 6PROCNO 1

F2 -­ Acquisition ParametersDate_ 20120808Time 21.47INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zg30TD 32768SOLVENT CDCl3NS 4DS 0SWH 7246.377 HzFIDRES 0.221142 HzAQ 2.2611110 secRG 256DW 69.000 usecDE 6.50 usecTE 297.3 KD1 2.00000000 secTD0 1

======== CHANNEL f1 ========NUC1 1HP1 11.70 usecPL1 4.00 dBSFO1 400.1324008 MHz

F2 -­ Processing parametersSI 16384SF 400.1300000 MHzWDW EMSSB 0LB 0 HzGB 0PC 1.00

1H

200 180 160 140 120 100 80 60 40 20 ppm

18.33

28.23

28.44

29.03

32.52

69.57

73.33

76.68

77.00

77.32

88.71

177.58 Current Data Parameters

NAME amy20120712EXPNO 3PROCNO 1

F2 -­ Acquisition ParametersDate_ 20120712Time 21.57INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zgpg30TD 32768SOLVENT CDCl3NS 59DS 0SWH 24038.461 HzFIDRES 0.733596 HzAQ 0.6816452 secRG 4096DW 20.800 usecDE 6.50 usecTE 298.5 KD1 2.00000000 secD11 0.03000000 secTD0 1

======== CHANNEL f1 ========NUC1 13CP1 8.90 usecPL1 7.00 dBSFO1 100.6233325 MHz

======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 3.80 dBPL12 21.60 dBPL13 24.60 dBSFO2 400.1316005 MHz

F2 -­ Processing parametersSI 32768SF 100.6127752 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.00

Copies of all 1H and 13C NMR Spectra

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 3: SupportingInformation Diastereoselective Synthesis of Vicinal · P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 Processing parameters SI 16384 ... Date_ 20120712 Time 21.57 INSTRUM

S3

10 9 8 7 6 5 4 3 2 1 0 ppm

1.6284

1.6339

1.6426

1.6500

1.6600

1.6702

1.6934

1.7003

1.7536

1.7632

1.7707

1.7798

1.8580

1.8706

1.8794

1.8862

1.9002

1.9092

2.0648

2.5614

2.5714

2.5838

2.5957

2.6011

2.6185

2.6320

3.7324

3.7419

3.7513

3.7604

3.7697

7.2594

3.054

4.130

2.028

2.012

1.000

3.087

1.001

Current Data ParametersNAME tryEXPNO 22PROCNO 1

F2 -­ Acquisition ParametersDate_ 20120929Time 16.05INSTRUM spectPROBHD 5 mm PABBO BB-­PULPROG zg30TD 32768SOLVENT CDCl3NS 4DS 0SWH 9057.971 HzFIDRES 0.276427 HzAQ 1.8088988 secRG 362DW 55.200 usecDE 6.50 usecTE 299.7 KD1 2.00000000 secTD0 1

======== CHANNEL f1 ========NUC1 1HP1 14.00 usecPL1 0 dBSFO1 500.1330008 MHz

F2 -­ Processing parametersSI 16384SF 500.1300129 MHzWDW EMSSB 0LB 0 HzGB 0PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

19.41

19.51

28.20

28.66

29.58

33.98

72.44

74.30

89.98

177.45 Current Data Parameters

NAME amy20120921EXPNO 5PROCNO 1

F2 -­ Acquisition ParametersDate_ 20120921Time 12.38INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zgpg30TD 32768SOLVENT DMSONS 109DS 0SWH 24038.461 HzFIDRES 0.733596 HzAQ 0.6816452 secRG 9195.2DW 20.800 usecDE 6.50 usecTE 299.0 KD1 2.00000000 secD11 0.03000000 secTD0 1

======== CHANNEL f1 ========NUC1 13CP1 8.90 usecPL1 7.00 dBSFO1 100.6233325 MHz

======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 3.80 dBPL12 21.60 dBPL13 24.60 dBSFO2 400.1316005 MHz

F2 -­ Processing parametersSI 32768SF 100.6127690 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.00

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 4: SupportingInformation Diastereoselective Synthesis of Vicinal · P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 Processing parameters SI 16384 ... Date_ 20120712 Time 21.57 INSTRUM

S4

10 9 8 7 6 5 4 3 2 1 0 ppm

1.471

1.486

1.556

1.586

1.617

1.649

1.686

1.747

1.853

1.878

1.891

1.894

1.905

1.916

1.925

1.939

1.948

1.970

2.243

2.474

2.489

2.502

2.512

2.527

2.535

2.544

2.551

2.554

2.558

2.578

2.597

2.774

3.625

3.631

4.114

4.124

4.132

4.143

4.150

4.161

3.057

3.041

2.055

1.020

1.097

0.802

1.047

0.981

3.059

0.968

1.008

1.000

Current Data ParametersNAME amy20120921EXPNO 7PROCNO 1

F2 -­ Acquisition ParametersDate_ 20120921Time 21.26INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zg30TD 32768SOLVENT CDCl3NS 4DS 0SWH 7246.377 HzFIDRES 0.221142 HzAQ 2.2611110 secRG 181DW 69.000 usecDE 6.50 usecTE 298.9 KD1 2.00000000 secTD0 1

======== CHANNEL f1 ========NUC1 1HP1 11.70 usecPL1 4.00 dBSFO1 400.1324008 MHz

F2 -­ Processing parametersSI 16384SF 400.1300056 MHzWDW EMSSB 0LB 0 HzGB 0PC 1.00

1H

200 180 160 140 120 100 80 60 40 20 ppm

27.54

27.61

31.06

31.18

33.16

39.65

43.39

67.00

72.44

76.68

77.00

77.32

88.42

177.58 Current Data Parameters

NAME amy20120809EXPNO 6PROCNO 1

F2 -­ Acquisition ParametersDate_ 20120809Time 19.26INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zgpg30TD 32768SOLVENT CDCl3NS 52DS 0SWH 24038.461 HzFIDRES 0.733596 HzAQ 0.6816452 secRG 4096DW 20.800 usecDE 6.50 usecTE 298.1 KD1 2.00000000 secD11 0.03000000 secTD0 1

======== CHANNEL f1 ========NUC1 13CP1 8.90 usecPL1 7.00 dBSFO1 100.6233325 MHz

======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 3.80 dBPL12 21.60 dBPL13 24.60 dBSFO2 400.1316005 MHz

F2 -­ Processing parametersSI 32768SF 100.6127775 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.00

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 5: SupportingInformation Diastereoselective Synthesis of Vicinal · P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 Processing parameters SI 16384 ... Date_ 20120712 Time 21.57 INSTRUM

S5

10 9 8 7 6 5 4 3 2 1 0 ppm

1.774

1.785

1.795

1.811

1.821

1.829

1.846

1.856

1.863

1.874

1.893

1.900

1.905

1.910

1.917

1.923

1.926

1.943

1.954

1.958

1.961

1.970

1.978

2.003

2.017

2.032

2.039

2.053

2.065

2.075

2.086

2.098

2.489

2.506

2.523

2.778

2.862

3.159

3.227

3.715

4.095

6.184

2.288

3.136

2.037

1.000

1.009

1.005

1.007

Current Data ParametersNAME gunEXPNO 28PROCNO 1

F2 -­ Acquisition ParametersDate_ 20101012Time 23.10INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zg30TD 16384SOLVENT CDCl3NS 8DS 0SWH 6009.615 HzFIDRES 0.366798 HzAQ 1.3632820 secRG 128DW 83.200 usecDE 6.50 usecTE 299.8 KD1 1.50000000 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 1HP1 11.20 usecPL1 0 dBSFO1 400.1326008 MHz

F2 -­ Processing parametersSI 16384SF 400.1300021 MHzWDW EMSSB 0LB 0.10 HzGB 0PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

15.85

18.12

27.89

28.90

29.80

31.78

68.66

73.41

85.98

171.35 Current Data Parameters

NAME gunEXPNO 7PROCNO 1

F2 -­ Acquisition ParametersDate_ 20100902Time 22.34INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zgpg30TD 65536SOLVENT CDCl3NS 123DS 0SWH 25062.656 HzFIDRES 0.382426 HzAQ 1.3075131 secRG 10240DW 19.950 usecDE 6.50 usecTE 299.6 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 13CP1 10.00 usecPL1 5.00 dBSFO1 100.6242995 MHz

======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 4.00 dBPL12 20.80 dBPL13 23.80 dBSFO2 400.1319000 MHz

F2 -­ Processing parametersSI 32768SF 100.6127672 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 6: SupportingInformation Diastereoselective Synthesis of Vicinal · P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 Processing parameters SI 16384 ... Date_ 20120712 Time 21.57 INSTRUM

S6

10 9 8 7 6 5 4 3 2 1 0 ppm

1.519

1.540

1.556

1.570

1.601

1.713

1.725

1.734

1.746

1.757

1.771

1.778

1.810

1.828

1.845

1.864

1.879

1.891

1.900

1.918

1.935

1.944

1.958

1.968

1.980

1.990

1.999

2.482

2.492

2.500

2.508

2.517

2.525

3.441

3.674

4.206

4.227

4.235

3.137

3.096

4.184

1.085

2.985

2.025

2.038

1.067

1.000

Current Data ParametersNAME gunEXPNO 3PROCNO 1

F2 -­ Acquisition ParametersDate_ 20100902Time 22.21INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zg30TD 16384SOLVENT CDCl3NS 1DS 0SWH 6009.615 HzFIDRES 0.366798 HzAQ 1.3632820 secRG 35.9DW 83.200 usecDE 6.50 usecTE 299.4 KD1 1.50000000 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 1HP1 8.80 usecPL1 0 dBSFO1 400.1326008 MHz

F2 -­ Processing parametersSI 16384SF 400.1299940 MHzWDW EMSSB 0LB 0.10 HzGB 0PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

15.63

27.87

29.41

30.31

31.09

33.91

39.94

43.42

66.25

72.87

86.64

171.37 Current Data Parameters

NAME gunEXPNO 4PROCNO 1

F2 -­ Acquisition ParametersDate_ 20100902Time 22.25INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zgpg30TD 65536SOLVENT CDCl3NS 31DS 0SWH 25062.656 HzFIDRES 0.382426 HzAQ 1.3075131 secRG 10240DW 19.950 usecDE 6.50 usecTE 299.6 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 13CP1 10.00 usecPL1 5.00 dBSFO1 100.6242995 MHz

======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 4.00 dBPL12 20.80 dBPL13 23.80 dBSFO2 400.1319000 MHz

F2 -­ Processing parametersSI 32768SF 100.6127672 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 7: SupportingInformation Diastereoselective Synthesis of Vicinal · P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 Processing parameters SI 16384 ... Date_ 20120712 Time 21.57 INSTRUM

S7

10 9 8 7 6 5 4 3 2 1 0 ppm

1.512

1.524

1.536

1.548

1.558

1.583

1.591

1.601

1.613

1.625

1.636

1.645

1.662

1.678

1.693

1.710

1.851

1.865

1.881

1.899

1.917

1.934

1.947

2.051

2.071

2.082

2.091

2.102

2.122

3.260

3.554

3.560

3.764

3.785

3.788

3.805

3.821

3.843

3.953

3.965

3.983

7.299

1.035

6.177

2.094

1.044

2.122

1.000

2.014

1.027

Current Data ParametersNAME 20100403-­2EXPNO 1PROCNO 1

F2 -­ Acquisition ParametersDate_ 20100403Time 17.12INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zg30TD 16384SOLVENT CDCl3NS 12DS 0SWH 5995.204 HzFIDRES 0.365918 HzAQ 1.3664756 secRG 22.6DW 83.400 usecDE 8.00 usecTE 301.3 KD1 1.50000000 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 1HP1 10.00 usecPL1 0 dBSFO1 400.1326008 MHz

F2 -­ Processing parametersSI 16384SF 400.1299933 MHzWDW EMSSB 0LB 0.10 HzGB 0PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

19.24

25.50

28.15

31.63

33.51

67.39

69.83

74.48

84.89

Current Data ParametersNAME 20100403-­2EXPNO 2PROCNO 1

F2 -­ Acquisition ParametersDate_ 20100403Time 17.15INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zgpg30TD 65536SOLVENT CDCl3NS 41DS 0SWH 25125.629 HzFIDRES 0.383387 HzAQ 1.3042164 secRG 4096DW 19.900 usecDE 8.00 usecTE 301.5 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 13CP1 8.90 usecPL1 5.00 dBSFO1 100.6243390 MHz

======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 100.00 usecPL2 0 dBPL12 19.10 dBPL13 22.10 dBSFO2 400.1319000 MHz

F2 -­ Processing parametersSI 32768SF 100.6127756 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 8: SupportingInformation Diastereoselective Synthesis of Vicinal · P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 Processing parameters SI 16384 ... Date_ 20120712 Time 21.57 INSTRUM

S8

10 9 8 7 6 5 4 3 2 1 0 ppm

1.254

1.372

1.381

1.403

1.411

1.444

1.480

1.492

1.523

1.554

1.561

1.581

1.594

1.599

1.612

1.631

1.814

1.831

1.849

1.867

1.885

2.067

2.086

2.099

2.104

2.117

2.136

3.193

3.504

3.796

3.813

3.830

4.073

4.080

4.090

4.102

4.109

3.024

3.017

1.057

4.070

2.008

1.007

2.085

1.000

2.016

1.006

Current Data ParametersNAME 20100608EXPNO 1PROCNO 1

F2 -­ Acquisition ParametersDate_ 20100608Time 14.35INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zg30TD 16384SOLVENT CDCl3NS 4DS 0SWH 6009.615 HzFIDRES 0.366798 HzAQ 1.3632820 secRG 32DW 83.200 usecDE 6.50 usecTE 299.4 KD1 1.50000000 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 1HP1 14.50 usecPL1 5.20 dBSFO1 400.1326008 MHz

F2 -­ Processing parametersSI 16384SF 400.1299999 MHzWDW EMSSB 0LB 0.10 HzGB 0PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

24.92

27.56

31.68

33.99

36.19

40.53

42.61

67.96

67.99

73.92

85.52

Current Data ParametersNAME 20100608EXPNO 2PROCNO 1

F2 -­ Acquisition ParametersDate_ 20100608Time 14.37INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zgpg30TD 65536SOLVENT CDCl3NS 59DS 0SWH 25062.656 HzFIDRES 0.382426 HzAQ 1.3075131 secRG 4096DW 19.950 usecDE 6.50 usecTE 299.6 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 13CP1 10.00 usecPL1 5.00 dBSFO1 100.6242995 MHz

======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 90.00 usecPL2 4.00 dBPL12 20.80 dBPL13 23.80 dBSFO2 400.1319000 MHz

F2 -­ Processing parametersSI 32768SF 100.6127478 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40

O

OHOH

23

O

OHOH

23

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 9: SupportingInformation Diastereoselective Synthesis of Vicinal · P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 Processing parameters SI 16384 ... Date_ 20120712 Time 21.57 INSTRUM

S9

10 9 8 7 6 5 4 3 2 1 0 ppm

1.688

1.699

1.706

1.719

1.727

1.748

1.790

1.798

1.807

1.816

1.823

1.832

1.846

1.856

1.865

1.875

2.083

2.114

2.122

2.145

2.153

2.245

2.273

2.422

2.447

2.460

2.472

2.492

2.524

2.556

2.567

3.236

3.252

3.258

3.274

3.280

3.296

3.308

3.318

3.327

3.339

3.349

4.170

4.176

4.503

4.513

4.522

7.290

7.310

7.749

7.770

8.708

1.002

0.973

3.077

0.965

2.052

1.001

1.000

2.127

2.024

Current Data ParametersNAME nitrileEXPNO 111PROCNO 1

F2 -­ Acquisition ParametersDate_ 20090921Time 22.51INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zg30TD 16384SOLVENT CDCl3NS 1DS 0SWH 5995.204 HzFIDRES 0.365918 HzAQ 1.3664756 secRG 128DW 83.400 usecDE 6.50 usecTE 299.4 KD1 1.50000000 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 1HP1 10.00 usecPL1 0 dBSFO1 400.1326008 MHz

F2 -­ Processing parametersSI 16384SF 400.1300061 MHzWDW EMSSB 0LB 0.10 HzGB 0PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

18.45

21.46

23.25

30.31

32.02

34.90

49.41

70.81

72.75

73.46

127.11

129.60

138.15

143.14 Current Data Parameters

NAME nitrileEXPNO 32PROCNO 1

F2 -­ Acquisition ParametersDate_ 20090731Time 22.24INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zgpg30TD 65536SOLVENT CDCl3NS 101DS 0SWH 25062.656 HzFIDRES 0.382426 HzAQ 1.3074932 secRG 4096DW 19.950 usecDE 6.50 usecTE 299.5 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 13CP1 8.90 usecPL1 5.00 dBSFO1 100.6243390 MHz

======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 100.00 usecPL2 0 dBPL12 19.10 dBPL13 22.10 dBSFO2 400.1319000 MHz

F2 -­ Processing parametersSI 32768SF 100.6127714 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

Page 10: SupportingInformation Diastereoselective Synthesis of Vicinal · P1 11.70 usec PL1 4.00 dB SFO1 400.1324008 MHz F2 Processing parameters SI 16384 ... Date_ 20120712 Time 21.57 INSTRUM

S10

10 9 8 7 6 5 4 3 2 1 0 ppm

1.470

1.511

1.547

1.579

1.698

1.714

1.728

1.741

1.755

1.762

1.792

1.798

1.862

1.880

1.899

1.909

1.922

1.938

1.956

2.134

2.327

2.339

2.373

2.430

2.655

2.680

2.695

2.710

2.720

3.109

3.127

3.148

3.166

3.348

3.363

3.377

3.384

3.400

4.216

4.540

4.551

4.561

7.261

7.296

7.316

7.750

7.770

3.169

3.147

1.076

1.116

2.151

2.087

0.974

2.136

2.916

1.015

1.068

1.063

1.000

1.054

2.090

2.075

Current Data ParametersNAME 990511EXPNO 12PROCNO 1

F2 -­ Acquisition ParametersDate_ 20100512Time 1.36INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zg30TD 16384SOLVENT CDCl3NS 8DS 0SWH 5995.204 HzFIDRES 0.365918 HzAQ 1.3664756 secRG 22DW 83.400 usecDE 8.00 usecTE 299.4 KD1 2.00000000 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 1HP1 10.00 usecPL1 0 dBSFO1 400.1326008 MHz

F2 -­ Processing parametersSI 16384SF 400.1300090 MHzWDW EMSSB 0LB 0.10 HzGB 0PC 1.00

200 180 160 140 120 100 80 60 40 20 ppm

21.41

24.10

28.61

31.91

34.71

34.98

42.07

47.76

48.48

71.70

73.28

73.79

127.16

129.45

138.07

142.99 Current Data Parameters

NAME nitrileEXPNO 153PROCNO 1

F2 -­ Acquisition ParametersDate_ 20091029Time 21.35INSTRUM spectPROBHD 5 mm BBO BB-­1HPULPROG zgpg30TD 65536SOLVENT CDCl3NS 47DS 0SWH 25062.656 HzFIDRES 0.382426 HzAQ 1.3074932 secRG 10240DW 19.950 usecDE 6.50 usecTE 299.3 KD1 2.00000000 secd11 0.03000000 secDELTA 1.89999998 secMCREST 0 secMCWRK 0.01500000 sec

======== CHANNEL f1 ========NUC1 13CP1 8.90 usecPL1 5.00 dBSFO1 100.6243390 MHz

======== CHANNEL f2 ========CPDPRG2 waltz16NUC2 1HPCPD2 100.00 usecPL2 0 dBPL12 19.10 dBPL13 22.10 dBSFO2 400.1319000 MHz

F2 -­ Processing parametersSI 32768SF 100.6127760 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.40

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013