A two-step synthesis of α-keto vinyl carbinols from ketones.

Abstract : Conjugate addition of lithium enolates onto terminal alkynyl- and allenyl-sulfoxides furnishes the corresponding allylic sulfoxides. The latter readily undergo a Mislow-Braverman-Evans rearrangement to yield the targeted α-keto vinyl carbinols. This two-step procedure does not require purification of the intermediates and constitutes the shortest approach to α-keto vinyl carbinols.
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Submitted on : Wednesday, March 26, 2014 - 9:39:01 PM
Last modification on : Thursday, February 7, 2019 - 5:16:41 PM

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Laurent Debien, Samir Z Zard. A two-step synthesis of α-keto vinyl carbinols from ketones.. Organic Letters, American Chemical Society, 2013, 15 (23), pp.6066-6069. ⟨10.1021/ol4029594⟩. ⟨hal-00966612⟩

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