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Favorskii rearrangement of a highly functionalized meso-dihaloketone

Abstract:

This paper describes studies on the feasibility of an asymmetric Favorskii rearrangement of a meso-dihaloketone substrate. In the racemic series, metal amide bases in the presence of amines give poor to reasonable yields of ring-contracted unsaturated cyclopentyl amides, whilst amines in aqueous solvent mixtures afford cyclopentyl amides in good to excellent yields. A range of chiral non-racemic amines are screened, a tiny diastereo-bias is observed and a tentative mechanistic rationale for t...

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Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON-ASYMMETRY
Volume:
20
Issue:
6-8
Pages:
961-969
Publication date:
2009-05-07
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
URN:
uuid:c7f685f7-49f9-4e27-96f7-72bbd5b3532a
Source identifiers:
58764
Local pid:
pubs:58764
Language:
English

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