Recent Developments in the Transfer of Chirality within Enolate Alkylation Reactions

Remarkable asymmetric induction is observed in the alkylation of enolates derived from enantiomerically pure amides, even though these enolates seem to have no apparent chirality (see scheme). The proposed origin and mechanism for this transfer of chirality is discussed. LTMP=lithium tetramethylpipe...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-12, Vol.44 (2), p.186-189
Main Authors: Eames, Jason, Suggate, Michael J.
Format: Article
Language:English
Subjects:
alkylation
asymmetric synthesis
conformational chirality
enantioselectivity
enolates
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Summary:Remarkable asymmetric induction is observed in the alkylation of enolates derived from enantiomerically pure amides, even though these enolates seem to have no apparent chirality (see scheme). The proposed origin and mechanism for this transfer of chirality is discussed. LTMP=lithium tetramethylpiperidide.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200461617