Regio??and Diastereoselective Copper (I)??Catalyzed Allylic Substitution of δ??Hydroxy Allylic Chlorides by a Silicon Nucleophile

CK Hazra, E Irran, M Oestreich

Index: Hazra, Chinmoy K.; Irran, Elisabeth; Oestreich, Martin European Journal of Organic Chemistry, 2013 , # 22 p. 4903 - 4908

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Citation Number: 7

Abstract

Abstract A perfectly γ-selective copper (I)-catalyzed allylic substitution of protected δ-hydroxy allylic chlorides with a silicon nucleophile generated by Si–B bond activation provides diastereoselective access to β-hydroxy α-chiral allylic silanes with an anti relative configuration. The high levels of diastereocontrol of this rare allylic displacement are interpreted according to a model suggested by Nakamura where diastereofacial selectivity ...