Enantiopure Bicyclic Piperidinones: Stereocontrolled Cycloadditions

A.   G.   Brewster; S.      Broady; E.      Glenn; S.   A.   Hermitage; M.      Hughes; M.   G.   Moloney; G.      Woods

doi:10.2174/1570178053400270

Abstract

The cycloadditions of a [4.3.0]-bicyclic α,β-unsaturated lactam, derived from 6-oxopipecolic acid, have been investigated. Although yields are modest, diastereoselectivity is high; reasons for the low reactivity are postulated, based on experimental observations and molecular modelling.

Keywords: piperidinones, conjugate additions, lewis acid catalysis

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Letters in Organic Chemistry

Title: Enantiopure Bicyclic Piperidinones: Stereocontrolled Cycloadditions

Volume: 2 Issue: 1

Author(s): A. G. Brewster, S. Broady, E. Glenn, S. A. Hermitage, M. Hughes, M. G. Moloney and G. Woods

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Keywords: piperidinones, conjugate additions, lewis acid catalysis

Abstract: The cycloadditions of a [4.3.0]-bicyclic α,β-unsaturated lactam, derived from 6-oxopipecolic acid, have been investigated. Although yields are modest, diastereoselectivity is high; reasons for the low reactivity are postulated, based on experimental observations and molecular modelling.

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Brewster G. A., Broady S., Glenn E., Hermitage A. S., Hughes M., Moloney G. M. and Woods G., Enantiopure Bicyclic Piperidinones: Stereocontrolled Cycloadditions, Letters in Organic Chemistry 2005; 2 (1) . https://dx.doi.org/10.2174/1570178053400270