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Convergent synthesis of stereodefined exo-alkylidene-gamma-lactams from beta-halo allylic alcohols.

ABSTRACT: A convergent process for the assembly of stereodefined mono- and bicyclic exo-alkylidene-gamma-lactams is described that proceeds through the union of beta-halo allylic alcohols, aromatic imines, and CO. Overall, regio- and stereoselective Ti-mediated reductive cross-coupling, followed by Pd-catalyzed carbonylation, can be performed in a one- or two-pot procedure, defining a highly selective three-component coupling process for heterocycle synthesis.

SUBMITTER: Umemura S

PROVIDER: S-EPMC2787655 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Convergent synthesis of stereodefined exo-alkylidene-gamma-lactams from beta-halo allylic alcohols.

Umemura Shuhei S McLaughlin Martin M Micalizio Glenn C GC

Organic letters 20091201 23

A convergent process for the assembly of stereodefined mono- and bicyclic exo-alkylidene-gamma-lactams is described that proceeds through the union of beta-halo allylic alcohols, aromatic imines, and CO. Overall, regio- and stereoselective Ti-mediated reductive cross-coupling, followed by Pd-catalyzed carbonylation, can be performed in a one- or two-pot procedure, defining a highly selective three-component coupling process for heterocycle synthesis. ...[more]

PMID: 19877599

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