Tandem Aza[4 + 2]/Allylboration: A Novel Multicomponent Reaction for the Stereocontrolled Synthesis of α-Hydroxyalkyl Piperidine Derivatives
- 27 October 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (23) , 3715-3718
- https://doi.org/10.1021/ol006626b
Abstract
The alpha-hydroxyalkyl piperidine unit is common to several naturally occurring alkaloids and azasugar analogues. Polysubstituted piperidine derivatives of this kind (3), embodying four stereogenic centers, are formed in just a single operation from the highly stereocontrolled reaction of 4-borono-1-azadienes (1), maleimides, and aldehydes. This novel multicomponent reaction which affords as many as four elements of diversity should prove highly valuable in combinatorial chemistry and natural product synthesis.Keywords
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