Primary??Amine??Catalyzed Enantioselective Intramolecular Aldolizations

J Zhou, V Wakchaure, P Kraft…

Index: Zhou, Jian; Wakchaure, Vijay; Kraft, Philip; List, Benjamin Angewandte Chemie - International Edition, 2008 , vol. 47, # 40 p. 7656 - 7658

Full Text: HTML

Citation Number: 134

Abstract

The enantioselective aldol cyclodehydration of 4-substituted 2, 6-heptandiones 1 to cyclohexenones 2 [eg, 1d to 2d, Eq.(1)] has been a long-term challenge in asymmetric catalysis. Pioneering investigations by Agami et al.[1] using proline catalysis, in analogy to the Hajos–Parrish–Eder–Sauer–Wiechert reaction,[2] have led to only moderate enantioselectivity and poor yields. Catalytic antibody 38C2, developed by Lerner, Barbas ...