Facile Synthesis of Chiral α-Difluoromethyl Amines from N-(tert-Butylsulfinyl)aldimines

Authors

  • Ya Li,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Feng-Lin Rd., Shanghai, 200032, China, Fax: (+86) 21-64166128
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  • Jinbo Hu Prof. Dr.

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Feng-Lin Rd., Shanghai, 200032, China, Fax: (+86) 21-64166128
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  • 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.

Abstract

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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.

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