Magnesium bromide promoted Barbier-type intramolecular cyclization of halo-substituted acetals, ketals, and orthoesters
Resource
Tetrahedron Letters 40 (49): 8647-8650
Journal
Tetrahedron Letters
Journal Volume
40
Journal Issue
49
Pages
8647-8650
Date Issued
1999
Date
1999
Author(s)
Abstract
Although acetals, ketals and orthoesters are commonly used as protective groups against organometallic reagents, Grignard reagents derived from halo-acetals, ketals, or orthoesters cyclize intramolecularly under MgBr2 promoted conditions, giving rise to the corresponding cycloalkanol and cycloalkanone derivatives. Our results also suggest a Lewis acid catalyzed push-pull mechanism operating for the cyclization.
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Type
journal article
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