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Novel copper hydride-promoted 1,3-rearrangement of α-allenylcyclopropane systems to methylenecyclopentenes

✍ Scribed by Kunio Hiroi; Fumiko Kato; Takamasa Oguchi; Shinya Saito; Takanori Sone

Book ID: 104095313
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 93 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.04.031

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✦ Synopsis

a-Allenylcyclopropanedicarboxylates, for which a novel synthetic method has been devised by conjugate addition of a copper hydride (Stryker) reagent to a-cyclopropylpropargylic esters, have been newly found to be smoothly converted to methylenecyclopentene derivatives under mild reaction conditions by further treatment with the copper hydride reagent. The mechanistic pathway is discussed.

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