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The first example for the asymmetric synthesis of allenes by the Doering–LaFlamme allene synthesis with enantiopure cyclopropylmagnesium carbenoids

✍ Scribed by Hitoshi Momochi; Takafumi Noguchi; Toshifumi Miyagawa; Naoki Ogawa; Makoto Tadokoro; Tsuyoshi Satoh

Book ID: 104099144
Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 637 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2011.03.150

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✦ Synopsis

The reaction of lithium a-sulfinyl carbanion of enantiopure dichloromethyl p-tolyl sulfoxide with a,bunsaturated carbonyl compounds gave optically active 1-chlorocyclopropyl p-tolyl sulfoxides having a carbonyl group with high asymmetric induction from the sulfur chiral center. Reduction of the carbonyl group followed by treatment with Grignard reagent, the 1-chlorocyclopropyl p-tolyl sulfoxides resulted in the formation of enantiopure allenic alcohols via the Doering-LaFlamme-type rearrangement of enantiopure cyclopropylmagnesium carbenoid intermediates. This is the first example for the asymmetric synthesis of allenes by the Doering-LaFlamme allene synthesis.

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