Indium-mediated Barbier-type allylation of aldehydes as a convenient method for the highly enantioselective synthesis of homoallylic alcohols

…, D Knueppel, D Steiner, K DeLaTorre, B Singaram

Index: Hirayama, Lacie C.; Gamsey, Soya; Knueppel, Daniel; Steiner, Derek; Delatorre, Kelly; Singaram, Bakthan Tetrahedron Letters, 2005 , vol. 46, # 13 p. 2315 - 2318

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Citation Number: 45

Abstract

We report a general method for the indium-mediated Barbier-type enantioselective allylation of both aromatic and aliphatic aldehydes using commercially available (1S, 2R)-(+)-2-amino- 1, 2-diphenylethanol as a chiral auxiliary. Using only two equivalents of allyl bromide, excellent yields and very good to excellent enantioselectivities are obtained. To our knowledge, the enantioselectivities reported herein are the highest obtained for indium- ...