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Prolylprolinol‐Catalyzed Asymmetric Michael Addition of Aliphatic Aldehydes to Nitroalkenes
Author(s) -
Lu Dengfu,
Gong Yuefa,
Wang Weizhou
Publication year - 2010
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.200900687
Subject(s) - chemistry , catalysis , stereoselectivity , michael reaction , catalytic efficiency , enantioselective synthesis , organocatalysis , organic chemistry , combinatorial chemistry
Several novel prolylprolinol catalysts have been designed and synthesized. This type of compound showed high catalytic efficiency on promoting the direct addition of unmodified aldehydes to nitroalkenes. Among the catalysts surveyed, the least bulky member ( 8d ) exhibited the best performance on both efficiency and stereoselectivity, providing the products with up to 97% ee value with 1.5–5 mol% catalyst loading. Additionally, computational studies of the transition state have been conducted to explain the high diastereo‐ and enantioselectivity.