- 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...
Expand abstract - Publication status:
- Published
- Publisher copy:
- 10.1016/j.tetasy.2009.03.020
-
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- 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
- Copyright date:
- 2009
Journal article
Favorskii rearrangement of a highly functionalized meso-dihaloketone
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