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Achiral Co‐Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts
Author(s) -
Ma Guangning,
Lin Shuangzheng,
Ibrahem Ismail,
Kubik Grzegorz,
Liu Leifeng,
Sun Junliang,
Córdova Armando
Publication year - 2012
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.201200357
Subject(s) - chemistry , stereocenter , catalysis , enantioselective synthesis , amine gas treating , combinatorial chemistry , organic chemistry , hydrogen bond , molecule
A stereochemical divergent approach for the highly enantioselective synthesis of distinct bicyclic products with multiple stereocenters from a racemate using a single chiral catalyst is disclosed. It is based on switches of the overall reaction pathways in the chiral amine‐catalyzed cascade reactions between racemic γ‐nitro ketones and α,β‐unsaturated aldehydes using different achiral co‐catalysts. The utility of the method is exemplified by the highly diasteroselective switch and stereoconvergent deracemization process by combination of chiral amine and achiral hydrogen‐bond‐donating catalysts.