Proline-Catalyzed Asymmetric Formal α-Alkylation of Aldehydes via Vinylogous Iminium Ion Intermediates Generated from Arylsulfonyl Indoles

Proline strikes again: The intermolecular enamine‐catalyzed asymmetric “formal” α‐alkylation of aldehydes is described. Alkylating reagent 1 generates a highly stabilized carbocation, which can readily intercept the enamine intermediate. L‐Proline proved to be the best catalyst, providing an easy ro...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-10, Vol.47 (45), p.8707-8710
Main Authors: Shaikh, Rafik R, Mazzanti, Andrea, Petrini, Marino, Bartoli, Giuseppe, Melchiorre, Paolo
Format: Article
Language:English
Subjects:
aldehydes
Aldehydes - chemical synthesis
Aldehydes - chemistry
Alkylation
Catalysis
Crystallography, X-Ray
Imines - chemistry
indoles
Indoles - chemistry
Ions - chemistry
Models, Molecular
Molecular Structure
organocatalysis
proline
Proline - chemistry
Stereoisomerism
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Summary:Proline strikes again: The intermolecular enamine‐catalyzed asymmetric “formal” α‐alkylation of aldehydes is described. Alkylating reagent 1 generates a highly stabilized carbocation, which can readily intercept the enamine intermediate. L‐Proline proved to be the best catalyst, providing an easy route to relevant 3‐indolyl derivatives 2 with high diastereo‐ and enantiocontrol.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200803947