Enantiopure bicyclic piperidinones: stereoselectivity in lactam enolate alkylations

The synthesis and alkylation of [4.3.0]-bicyclic lactams, derived from 6-oxopipecolic acid, have been investigated. Alkylation can proceed with predominantly exo-diastereoselectivity, but the efficiency of this process depends on the substitution at the hemiaminal ether system. These products can be...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2004-04, Vol.2 (7), p.1031-1043
Main Authors: Brewster, Andrew G, Broady, Simon, Davies, Catherine E, Heightman, Thomas D, Hermitage, Stephen A, Hughes, Mark, Moloney, Mark G, Woods, Gordon
Format: Article
Language:English
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Summary:The synthesis and alkylation of [4.3.0]-bicyclic lactams, derived from 6-oxopipecolic acid, have been investigated. Alkylation can proceed with predominantly exo-diastereoselectivity, but the efficiency of this process depends on the substitution at the hemiaminal ether system. These products can be readily deprotected to give substituted hydroxymethyl lactams in good yield.
ISSN:1477-0520
1477-0539
DOI:10.1039/b316037h