Asymmetric, organocatalytic, three-step synthesis of alpha-hydroxy-(E)-beta,gamma-unsaturated esters.
An efficient and enantiocontrolled three-step synthesis of alpha-hydroxy-(E)-beta,gamma-unsaturated esters is reported. Enantioenriched alpha-selenyl aldehydes, prepared in one step by asymmetric, organocatalytic alpha-selenylation of aldehydes, were directly subjected to a Wittig reaction followed by allylic selenide to selenoxide oxidation and final spontaneous [2,3]-sigmatropic rearrangement to yield the target compounds in 43-65% overall yield and in 94-97% ee.
Hess
Lindsey C
LC
Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
Posner
Gary H
GH
D002384:Catalysis; D004952:Esters; D009930:Organic Chemicals / Q000737:chemistry*
D004952:Esters; D009930:Organic Chemicals