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 | Zendy

Chang Chihliang | Zendy; Li SsuHsien | Zendy; Reddy Raju Jannapu | Zendy; Chen Kwunmin | Zendy

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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 ).

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