Three-Component Sequential Aza[4+2] Cycloaddition/Allylboration/Retro-Sulfinyl-Ene Reaction: A New Stereocontrolled Entry to Palustrine Alkaloids and Other 2,6-Disubstituted Piperidines

Step‐economy and stereocontrol are highlighted in a novel three‐component sequential reaction to access substituted piperidines (see scheme). Through combining boronate‐substituted hydrazonobutadienes, chiral sulfinimide dienophiles, and aldehydes in a highly regio‐ and diastereoselective fashion, a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-04, Vol.43 (15), p.2001-2004
Main Authors: Touré, Barry B., Hall, Dennis G.
Format: Article
Language:English
Subjects:
allylation
asymmetric synthesis
cycloaddition
multicomponent reactions
nitrogen heterocycles
piperidines
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Summary:Step‐economy and stereocontrol are highlighted in a novel three‐component sequential reaction to access substituted piperidines (see scheme). Through combining boronate‐substituted hydrazonobutadienes, chiral sulfinimide dienophiles, and aldehydes in a highly regio‐ and diastereoselective fashion, a concise synthesis of the palustrine derivative (−)‐methyl dihydropalustramate was accomplished.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353152