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Asymmetric Organocatalytic Four‐Component Quadruple Domino Reaction Initiated by Oxa‐Michael Addition of Alcohols to Acrolein
Author(s) -
Zhang FangLin,
Xu AiWen,
Gong YueFa,
Wei MoHui,
Yang XiangLiang
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900613
Subject(s) - iminium , enamine , chemistry , acrolein , michael reaction , diastereomer , cascade reaction , organocatalysis , cyclohexene , domino , component (thermodynamics) , cascade , catalysis , enantiomer , organic chemistry , stereochemistry , enantioselective synthesis , physics , chromatography , thermodynamics
Four‐component, quadruple cascade, one catalyst : An asymmetric four‐component (ABC 2 ) quadruple cascade reaction initiated by oxa‐Michael addition of aliphatic alcohols to acrolein is reported (see scheme) to provide high yields of trisubstituted highly functionalized cyclohexene carbaldehydes with excellent diastereomeric and complete enantiomeric control. This process can be explained by an iminium (Im)–enamine (En)–iminium (Im)–enamine (En) sequence mechanism.