2006

AminesQ 0120 Stereoselective Nucleophilic Monofluoromethylation of N-(tert-Butanesulfi-

nyl)imines with Fluoromethyl Phenyl Sulfone. — A highly stereoselective nucleo-philic monofluoromethylation of chiral sulfinylimines with fluoromethyl phenyl sul-fone is developed. The products are obtained in excellent yield with high stereoselec-tivity (99:1 or 98:2). Without purification, they are converted into α-monofluorometh-ylamine salts (VI) via reductive desulfonation and removal of the tert-butanesulfinyl group. The same methodology is also used to synthesize homochiral α-monofluoro-methylated cyclic secondary amines using tosylate-bearing (R)-(tert-butanesulfi-nyl)imine precursors (VII). — (LI, Y.; NI, C.; LIU, J.; ZHANG, L.; ZHENG, J.; ZHU, L.; HU*, J.; Org. Lett. 8 (2006) 8, 1693-1696; State Key Lab. Organofluorine Chem., Shanghai Inst. Org. Chem., Chin. Acad. Sci., Shanghai 200032, Peop. Rep. China; Eng.) — Bartels

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