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.
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