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Synthesis and reactions of 1,2-disubstituted methylenecyclopropanes prepared via intramolecular cyclopropanation of allenic diazoacetates

✍ Scribed by Mark Lautens; Christophe Meyer; Arjan van Oeveren

Book ID: 104257127
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 220 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00765-x

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✦ Synopsis

Diazoacetates derived from o~-or 13-allenic alcohols, prepared using the glyoxylic acid chloride p-toluenesulfonylhydrazone method, undergo regioselective intramolecular cyclopropanation in the presence of a copper (II) catalyst in refluxing toluene, leading to synthetically useful di-or trisubstituted methylenecyclopropyl lactones. The diastereoselectivity of the process has been studied.

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