Water in Stereoselective Organocatalytic Reactions

In this review, recent advances in asymmetric organocatalytic reactions carried out with variable amounts of water, from substoichiometric to a large excess (reaction medium), are discussed. We also summarize several proposed mechanisms for the different possibilities of the action of water both in...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2009-01, Vol.351 (1-2), p.33-57
Main Authors: Gruttadauria, Michelangelo, Giacalone, Francesco, Noto, Renato
Format: Article
Language:English
Subjects:
aldol reaction
Diels-Alder reaction
Mannich reaction
Michael addition
organic catalysis
water
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Summary:In this review, recent advances in asymmetric organocatalytic reactions carried out with variable amounts of water, from substoichiometric to a large excess (reaction medium), are discussed. We also summarize several proposed mechanisms for the different possibilities of the action of water both in the increased activity of the catalyst and in the asymmetric induction. Finally, the application of this catalytic methodology to the enantioselective synthesis of valuable compounds through enamine or iminium catalysis is presented.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200800731