ChemInform Abstract: Redox‐Triggered C—C Coupling of Alcohols and Vinyl Epoxides: Diastereo‐ and Enantioselective Formation of All‐Carbon Quaternary Center via tert‐(Hydroxy)‐Prenylation.

Abstract

Redox-Triggered C-C Coupling of Alcohols and Vinyl Epoxides: Diastereoand Enantioselective Formation of All-Carbon Quaternary Center via tert--(Hydroxy)-Prenylation.-The same products are prepared starting from oxirane substrates and alcohols or aldehydes, in the latter case requiring the addition of iPrOH. The transformation of (XII) in the presence of the catalyst with the opposite chirality yields the corresponding stereoisomer of (XIII) with high diastereoselectivity. -(FENG, J.; GARZA, V. J.; KRISCHE*, M. J.; J. Am. Chem. Soc. 136 (2014) 25, 8911-8914, http://dx.doi.org/10.1021/ja504625m ; Dep. Chem., Univ. Tex., Austin, TX 78712, USA; Eng.) -F. Schill