Journal article
Preparation of spirocyclic cyclopropyl ketones through condensation of epoxides with .beta.-keto phosphonates
Journal of organic chemistry, Vol.58(17), pp.4584-4588
08/01/1993
DOI: 10.1021/jo00069a018
Abstract
The β-keto phosphonate derivatives of several cyclic ketones have been shown to undergo condensation with epoxides upon treatment with base, affording spirocyclic cyclopropyl ketones. Moderate to reasonable yields were obtained under sealed tube conditions with ethylene oxide, propylene oxide, and styrene oxide, and the substituted epoxides gave a single diastereomer in each case. The process can be viewed as an example of regiospecific geminal dialkylation, and cleavage of the cyclopropyl ring allows access to additional α,α-dialkylated ketones. © 1993, American Chemical Society. All rights reserved.
Details
- Title: Subtitle
- Preparation of spirocyclic cyclopropyl ketones through condensation of epoxides with .beta.-keto phosphonates
- Creators
- Thomas E JacksHeidi NibbeDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.58(17), pp.4584-4588
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00069a018
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 08/01/1993
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9984216573002771
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