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Enantio‐ and Diastereoselective Mannich‐Type Reactions of α‐Cyano Ketones with N ‐Boc Aldimines Catalyzed by Chiral Bifunctional Urea
Author(s) -
Lee Ju Hee,
Kim Dae Young
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900268
Subject(s) - aldimine , chemistry , bifunctional , enantioselective synthesis , electrophile , catalysis , mannich reaction , organic chemistry , organocatalysis
Abstract The catalytic enantioselective electrophilic Mannich‐type reaction promoted by chiral bifunctional organocatalysts is described. The treatment of α‐cyano ketones with N ‐Boc‐aldimines under mild reaction conditions afforded the corresponding β‐amino‐α‐cyano ketones with excellent diastereoselectivities (up to syn/anti =100/0), and excellent enantioselectivities (up to 99% ee ).