Enantioselective reduction of heteroaromatic β, γ-unsaturated ketones as an alternative to allylboration of aldehydes.: Application: asymmetric synthesis of SIB-1508Y

FX Felpin, MJ Bertrand, J Lebreton

Index: Felpin, Francois-Xavier; Bertrand, Marie-Jo; Lebreton, Jacques Tetrahedron, 2002 , vol. 58, # 37 p. 7381 - 7389

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Citation Number: 28

Abstract

This shows the importance of the control of chirality for the synthesis of new nAChR agonists. In connection with our efforts to investigate structure–activity relationships of nAChR ligands, we have recently reported the enantioselective synthesis of nicotine 1, 5 SIB-1508Y 2, 6 and other related piperidinic alkaloids. 7 The preparation of chiral homoallylic alcohols by enantioselective allylboration of aldehydes was a key step in our synthesis (Scheme1).