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A short synthesis of α-allenic alcohols from α,β-unsaturated carbonyl compounds with dichloromethyl p-tolyl sulfoxide

✍ Scribed by Tsuyoshi Satoh; Takafumi Noguchi; Toshifumi Miyagawa

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
188 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reaction of the a-sulfinyl carbanion of dichloromethyl p-tolyl sulfoxide with a,b-unsaturated carbonyl compounds gave 1-chlorocyclopropyl p-tolyl sulfoxides having a carbonyl group in good to high yields. The carbonyl groups in the products were reduced or treated with alkylmetals to give alcohols.

Finally, the alcohols were treated with Grignard reagent to give a-allenic alcohols via the rearrangement of the cyclopropylmagnesium carbenoid intermediates, which were generated by the sulfoxidemagnesium exchange reaction, in good to high yields. This procedure provides a new method for a short synthesis of various a-allenic alcohols in two or three steps from relatively easily available a,b-unsaturated carbonyl compounds.

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