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Chiral Lewis Base Catalyzed Highly Enantioselective Reduction of N ‐Alkyl β‐Enamino Esters with Trichlorosilane and Water
Author(s) -
Wu Xinjun,
Li Yang,
Wang Chao,
Zhou Li,
Lu Xiaoxia,
Sun Jian
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003105
Subject(s) - trichlorosilane , enantioselective synthesis , alkyl , chemistry , catalysis , reduction (mathematics) , base (topology) , lewis acids and bases , organic chemistry , mathematics , mathematical analysis , geometry , silicon
First, test the water! In the presence of a chiral Lewis base catalyst 2 , the supposedly moisture‐unfriendly reduction system with trichlorosilane was found to be highly efficient and enantioselective when using water as an additive. For the first time, this method enables the reduction of a broad range of N ‐alkyl β‐enamino esters 1 to give N ‐alkyl β‐amino esters 3 in good to high yields and with excellent enantioselectivities (see scheme).