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

Laurent Debien (1) , Samir Z Zard (1)

1 DCSO - Laboratoire de synthèse organique

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.

Domaines: Chimie organique

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