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Synfacts 2005(3): 0306-0306
DOI: 10.1055/s-2005-916133
DOI: 10.1055/s-2005-916133
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Enantiopure α-Difluoromethyl Amines from N-(tert-Butylsulfinyl)aldimines
Y. Li, J. Hu*
Shanghai Institute of Organic Chemistry, P. R. of China
Further Information
Publication History
Publication Date:
22 November 2005 (online)
Significance
Nucleophilic addition of (phenylsulfonyl)difluoromethyl anion (PhSO2CF2-) to N-(tert-butylsulfinyl)aldimines resulted in N-tert-butylsulfinyl-protected amines in good to excellent yields and excellent diastereoselectivity. A broad range of substrates were tolerated under the reaction conditions including aryl, hetereoaryl, and alkylaldimine bearing an α-hydrogen. Simultaneous removal of the tert-butylsulfinyl and phenylsulfonyl groups under reductive conditions (Na/Hg) gave the desired α-difluoromethyl amines, which were isolated as their HCl salts. This process conveniently produced a variety of enantiopure α-difluoromethyl amines from readily accessible starting materials.