Journal
TETRAHEDRON LETTERS
Volume 52, Issue 19, Pages 2468-2470Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.03.008
Keywords
Intramolecular Michael reaction; N-heterocyclic carbene; Aldehyde enolate; Bronsted base
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Funding
- Duke University
- NCBC [2008-IDG-1010]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0923097] Funding Source: National Science Foundation
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Due to the high reactivity of the formyl group under either basic or acidic reaction conditions required for the direct generation of aldehyde enolates, intramolecular Michael additions of aldehyde enolates to alpha,beta-unsaturated carbonyl compounds have been underexplored for the stereoselective synthesis of carbocyclic compounds. The intramolecular Michael reaction of aldehyde enolates generated by imidazolium carbenes was explored for the synthesis of cyclopentane aldehydes. The imidazolium carbenes were used as Bronsted bases to directly generate the aldehydes enolates. (C) 2011 Elsevier Ltd. All rights reserved.
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