Diastereoselectivity in the alkylations of bicyclic piperidinones

The synthesis of substituted [4.3.0] bicyclic lactams derived from 6-oxo-2-hydroxymethylpiperidine is described. The enolate derived from these systems can be alkylated with a range of reactive electrophiles; the diastereoselectivity which can be achieved depends on the substitution pattern of the o...

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Bibliographic Details
Published in:Tetrahedron letters 1998-02, Vol.39 (9), p.1025-1028
Main Authors: Mills (née Davis), Catherine E., Heightman, Thomas D., Hermitage, Stephen A., Moloney, Mark G., Woods, Gordon A.
Format: Article
Language:English
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Summary:The synthesis of substituted [4.3.0] bicyclic lactams derived from 6-oxo-2-hydroxymethylpiperidine is described. The enolate derived from these systems can be alkylated with a range of reactive electrophiles; the diastereoselectivity which can be achieved depends on the substitution pattern of the oxazolidine ring system and the nature of the alkylating reagent, and can vary from 1:1 to as much as 10:1. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)10694-3