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Convergent synthesis of piperidines by the union of conjugated alkynes with imines: a unique regioselective bond construction for heterocycle synthesis.

ABSTRACT: A two-step process is described for the union of aromatic imines, conjugated alkynes, and aldehydes that results in a stereoselective synthesis of highly substituted piperidines. This synthetic process has been made possible by defining a unique regioselective functionalization of conjugated alkynes that establishes a suitably functionalized substrate for subsequent heterocycle-forming cationic annulation. Given the flexibility of the coupling process, heterocycles can be accessed through a process that establishes up to four stereogenic centers and four fused rings.

SUBMITTER: Chen MZ

PROVIDER: S-EPMC2783831 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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Convergent synthesis of piperidines by the union of conjugated alkynes with imines: a unique regioselective bond construction for heterocycle synthesis.

Chen Ming Z MZ Micalizio Glenn C GC

Organic letters 20091101 21

A two-step process is described for the union of aromatic imines, conjugated alkynes, and aldehydes that results in a stereoselective synthesis of highly substituted piperidines. This synthetic process has been made possible by defining a unique regioselective functionalization of conjugated alkynes that establishes a suitably functionalized substrate for subsequent heterocycle-forming cationic annulation. Given the flexibility of the coupling process, heterocycles can be accessed through a proc ...[more]

PMID: 19817447

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