Intramolecular Cyclopropanation of Unsaturated Terminal Epoxides

Efficient lithium amide-induced intramolecular cyclopropanation of bishomoallylic and trishomoallylic epoxides is described. The methodology is used in an asymmetric synthesis of sabina ketone.

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 126; no. 28; pp. 8664 - 8665
Main Authors Hodgson, David M, Chung, Ying Kit, Paris, Jean-Marc
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.07.2004
Amer Chemical Soc
Subjects
Chemical reactivity
Chemistry
Chemistry, Multidisciplinary
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Epoxy Compounds - chemical synthesis
Epoxy Compounds - chemistry
Exact sciences and technology
Molecular Structure
Organic chemistry
Physical Sciences
Reactivity and mechanisms
Science & Technology
LITHIUM AMIDES
ALDEHYDES
CARBENOIDS
COMPLEXES
Cyclopropanation
Intramolecular reaction
Bicyclic compound
Three membered ring
Experimental study
Oxygen heterocycle
Ethylenic compound
Diastereoselectivity
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Summary:Efficient lithium amide-induced intramolecular cyclopropanation of bishomoallylic and trishomoallylic epoxides is described. The methodology is used in an asymmetric synthesis of sabina ketone.
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ark:/67375/TPS-SW8353H8-P
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja047346k