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A General Organocatalytic Enantioselective Malonate Addition to α,β‐Unsaturated Enones
Author(s) -
Wascholowski Veit,
Knudsen Kristian Rahbek,
Mitchell Claire E. T.,
Ley Steven V.
Publication year - 2008
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.200800673
Subject(s) - enantioselective synthesis , malonate , dimethyl malonate , chemistry , diethyl malonate , reagent , organic chemistry , conjugate , enantiomeric excess , enone , michael reaction , catalysis , addition reaction , combinatorial chemistry , mathematics , mathematical analysis
A general enantioselective organocatalytic conjugate addition procedure of a variety of malonates to α,β‐unsaturated enone systems is presented. The reaction is efficiently catalysed by the pyrrolidinyl tetrazole catalyst 1 . Cyclic, acyclic and aromatic enones can be used and the reaction with ethyl malonates 3 b provides the Michael addition products in high yields with good to excellent enantioselectivities. Since only 1.5 equivalents of malonate are used as a reagent, the reaction is readily scaled and practical to operate. Furthermore, the malonate addition products can be easily mono decarboxylated without loss in enantiomeric excess by enzymatic or sodium hydroxide mediated methods.