Enantioselective β??Vinylation of α, β??Unsaturated Aldehydes Using a β??Nitroethyl Sulfone as Vinyl Anion Equivalent

…, Á Puente, M Zalacain, C Palomo

Index: Gianelli, Chiara; Lopez, Rosa; Puente, Angel; Zalacain, Maitane; Palomo, Claudio European Journal of Organic Chemistry, 2012 , # 14 p. 2774 - 2779

Full Text: HTML

Citation Number: 3

Abstract

Abstract A concise method for the asymmetric β-vinylation of enals is presented. The success of the reaction lies in the stereoselective organocatalyzed addition of β-nitroethyl sulfone 1 to enals and in the ability of Mg to promote the concomitant elimination of the sulfone moiety and the nitrous acid. The method performed in a three-step one-pot operation allows the synthesis of enantioenriched β-vinyl aldehydes and derivatives thereof.