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Pyrrolidine‐Camphor Derivative as an Organocatalyst for Asymmetic Michael Additions of α,α‐Disubstituted Aldehydes to β‐Nitroalkenes: Construction of Quaternary Carbon‐Bearing Aldehydes under Solvent‐Free Conditions
Author(s) -
Chang Chihliang,
Li SsuHsien,
Reddy Raju Jannapu,
Chen Kwunmin
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.200800771
Subject(s) - chemistry , pyrrolidine , michael reaction , organocatalysis , camphor , organic chemistry , catalysis , benzoic acid , yield (engineering) , solvent , enantioselective synthesis , materials science , metallurgy
A novel pyrrolidine‐camphor organocatalyst 3 was designed, synthesized and proven to be an efficient catalyst for the asymmetric Michael reaction. Treatment of α,α‐disubstituted aldehydes with β‐nitroalkenes in the presence of 20 mol% organocatalyst 3 and 20 mol% benzoic acid under solvent‐free conditions provided the desired Michael product possessing an all‐carbon quaternary center with high chemical yields (up to 99% yield) and high levels of enantioselectivities (up to 95% ee ).