supplementary information - nature · supplementary information. doi: 10.1038/nchem.1971 si-1 ....

NATURE CHEMISTRY | www.nature.com/naturechemistry 68

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-68

(R)-3d 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

O

Ph

t-BuO2C

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NATURE CHEMISTRY | www.nature.com/naturechemistry 69

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-69

Chiral HPLC traces: racemic

Chiral HPLC traces: enantioenriched

min10.5 11 11.5 12 12.5 13 13.5

mAU

0

100

200

300

400

500

600

700

DAD1 C, Sig=210,8 Ref=360,100 (AMADEU\AB445000.D)

11.

286

12.

148

min11 11.5 12 12.5 13 13.5

mAU

0

100

200

300

400

500

600

DAD1 C, Sig=210,8 Ref=360,100 (AMADEU\AB445003.D)

11.

353

12.

238

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NATURE CHEMISTRY | www.nature.com/naturechemistry 70

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-70

(R)-4a   1H NMR (400 MHz, CDCl3)

13C NMR (100 MHz, CDCl3)

S

Ph

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NATURE CHEMISTRY | www.nature.com/naturechemistry 71

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-71

Chiral HPLC traces: racemic

Chiral HPLC traces: enantioenriched

min0 10 20 30 40 50 60 70 80 90

mAU

0

0.5

1

1.5

2

2.5

DAD1 B, Sig=254,16 Ref=360,100 (MARTIN\MOC85-4.D)

Area: 633

.011

76

.57

6

Area: 660

.554

85

.77

2

min0 20 40 60 80 100

mAU

0

5

10

15

20

25

30

DAD1 B, Sig=254,16 Ref=360,100 (MARTIN\MOC91.D)

Area: 923

4.12

76

.37

5

Area: 210

.822

87

.10

5

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NATURE CHEMISTRY | www.nature.com/naturechemistry 72

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-72

(R)-5d   1H NMR (400 MHz, CDCl3)

13C NMR (100 MHz, CDCl3)

O

Ph

CO2t-Bu

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NATURE CHEMISTRY | www.nature.com/naturechemistry 73

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-73

Chiral SFC traces: racemic

Chiral SFC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 74

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-74

(R)-6a 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

N

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 75

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-75

Chiral SFC traces: racemic

Chiral SFC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 76

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-76

6j 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

TBSOH

H

H H

H

N

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NATURE CHEMISTRY | www.nature.com/naturechemistry 77

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-77

(R)-7a 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

OMeMeO

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 78

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-78

Chiral SFC traces: racemic

Chiral SFC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 79

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-79

7i 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

HOH

H

H H

H

OMeMeO

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 80

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-80

(S)-7k 1H NMR (400 MHz, CDCl3)    

 13C NMR (100 MHz, CDCl3)

Ph

OMe

MeO

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 81

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-81

Chiral HPLC traces: racemic

Chiral HPLC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 82

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-82

(S)-7l 1H NMR (400 MHz, CDCl3)    

13C NMR (100 MHz, CDCl3)

Ph

OMe

MeO

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 83

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-83

Chiral HPLC traces: racemic

Chiral HPLC traces: enantioenriched

Chiral HPLC traces: enantioenriched + racemic

min0 2 4 6 8 10 12 14 16 18

mAU

0

50

100

150

200

250

300

350

400

DAD1 A, Sig=250,100 Ref=360,100 (MARTIN\MOD107R.D)

9.4

37

10.

963

min0 2 4 6 8 10 12 14 16 18

mAU

0

5

10

15

20

25

30

35

DAD1 A, Sig=250,100 Ref=360,100 (MARTIN\MOD165A1.D)

Area: 11

99.15

9.1

74

min0 2.5 5 7.5 10 12.5 15 17.5 20 22.5

mAU

0

100

200

300

400

500

DAD1 C, Sig=210,8 Ref=360,100 (MARTIN\MOC15000.D)

Area

: 814

4.78

9.4

69

Area

: 279

.214

10.

343

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NATURE CHEMISTRY | www.nature.com/naturechemistry 84

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-84

(R)-8a 1H NMR (400 MHz, CDCl3)

13C NMR (100 MHz, CDCl3)

Me2N

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 85

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-85

Chiral SFC traces: racemic

Chiral SFC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 86

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-86

8j 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

TBSOH

H

H H

H

NMe2

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NATURE CHEMISTRY | www.nature.com/naturechemistry 87

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-87

(R)-9a 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

MeO

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 88

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-88

Chiral SFC traces: racemic

Chiral SFC: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 89

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-89

(R)-10a 1H NMR (400 MHz, CDCl3)  

13C NMR (100 MHz, CDCl3)

Ph

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 90

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-90

Chiral HPLC traces: racemic

Chiral HPLC traces: enantioenriched

© 2014 Macmillan Publishers Limited. All rights reserved.

NATURE CHEMISTRY | www.nature.com/naturechemistry 96

SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971

SI-96  

Chiral SFC traces for B(pin)-11k: racemic

Chiral HPLC traces for B(pin)-11k: enantioenriched

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