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Enantiopure bicyclic piperidinones: stereocontrolled conjugate additions leading to substituted piperidinones.

Abstract:
The conjugate additions of Reformatsky reagents, organocuprate reagents, and hydroxylamines to a [4.3.0]-bicyclic enelactam derived from 6-oxopipecolic acid have been investigated, and found to be efficient, proceeding with excellent exo-stereocontrol, with the exception of N-benzyl-O-benzylhydroxylamine, which gives predominantly the product of endo-addition. These adducts can be readily converted to substituted piperidinones.
Publication status:
Published

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Publisher copy:
10.1039/b404325a

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic and biomolecular chemistry
Volume:
2
Issue:
12
Pages:
1800-1810
Publication date:
2004-06-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:d954fc6c-543b-4ce6-80af-220382acb094
Source identifiers:
32742
Local pid:
pubs:32742
Language:
English

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