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Axially Chiral Guanidine as Enantioselective Base Catalyst for 1,4-Addition Reaction of 1,3-Dicarbonyl Compounds with Conjugated Nitroalkenes

Journal of the American Chemical SocietyPublished 11 January 2006
Masahiro Terada, Hitoshi Ube, Yusuke Yaguchi
Citations236
SJR quartileQ1
SJR score5.55
SNIP2.61

TL;DR

The axially chiral guanidine catalysts thus developed facilitated the highly enantioselective 1,4-addition reaction of 1,3-dicarbonyl compounds with a broad range of conjugated nitroalkenes and showed extremely high catalytic activity.

Abstract

A new strategy for designing chiral guanidine molecules is presented, which features the introduction of an axially chiral binaphthyl backbone. The axially chiral guanidine catalysts thus developed facilitated the highly enantioselective 1,4-addition reaction of 1,3-dicarbonyl compounds with a broad range of conjugated nitroalkenes and showed extremely high catalytic activity.

Keywords

Chemistry