Dedicated to Prof. George A. Olah on the occasion of his receipt of the 2005 Priestley Medal. Support of our work by the “Hundreds Talent Program” from the Chinese Academy of Sciences is gratefully acknowledged.
Facile Synthesis of Chiral α-Difluoromethyl Amines from N-(tert-Butylsulfinyl)aldimines†
Article first published online: 8 SEP 2005
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 44, Issue 36, pages 5882–5886, September 12, 2005
How to Cite
Li, Y. and Hu, J. (2005), Facile Synthesis of Chiral α-Difluoromethyl Amines from N-(tert-Butylsulfinyl)aldimines. Angew. Chem. Int. Ed., 44: 5882–5886. doi: 10.1002/anie.200501769
- Issue published online: 8 SEP 2005
- Article first published online: 8 SEP 2005
- Manuscript Received: 23 MAY 2005
- synthetic methods
Nucleophilic (phenylsulfonyl)difluoromethylation of (R)-(N-tert-butylsulfinyl)aldimines with difluoromethyl phenyl sulfone affords the corresponding products in excellent yields and with high diastereoselectivity (see scheme). The facile and convenient deprotection of both tert-butylsulfinyl and phenylsulfonyl groups affords the target α-difluoromethyl amines with high enantiomeric purity.