Tetrahedron

Auto-protonation diastereoselective d'enolates issus de l'addition-1, 4 d'nethiolates avec des enones

S Berrada, S Desert, P Metzner

Index: Berrada, Sald; Desert, Stephane; Metzner, Patrick Tetrahedron, 1988 , vol. 44, # 12 p. 3575 - 3586

Full Text: HTML

Citation Number: 22

Abstract

1, 4-Addltion reaction of lithiated methyl dithioacetate with alpha,-beta-disubstituted enones affords diastereomeric 5-oxodithioalkanoates. Syn configuration was assigned to the major diastereomer by chemical correlation. High diastereoselectivities were obtained with 2, 2, 4- trimethyl-4-hexen-3 one and 2-ethylldenecycloalkanones, making this reaction useful for selective synthesis of acyclic or semi-cyclic chains with 1, 2-adjacent asymmetric carbons. ...