A mild and efficient approach to enantioenriched α-hydroxyethyl α,β-unsaturated δ-lactams

TETRAHEDRON LETTERS

卷:57

Article

Han, Seo-Jung¹  Stoltz, Brian M.¹ 

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, 1200 Calif Blvd,MC 101-20, Pasadena, CA 91125 USA

关键词: delta-Lactams;    Ring-closing metathesis;    Asymmetric allylation;    Baylis-Hillman reaction;   

DOI  :  10.1016/j.tetlet.2016.04.022

来源: Elsevier

【 摘 要 】

A straightforward approach toward enantioenriched a-substituted alpha,beta-unsaturated delta-lactams is described. Although a considerable number of approaches toward alpha,beta-unsaturated S-lactams have been reported, there are relatively few examples of enantioenriched alpha,delta-disubstituted alpha,beta-unsaturated delta-lactams formation. The delta-stereocenter was formed by addition of allylmagnesium bromide to an N-tent-butylsulfinyl imine. The alpha,beta-unsaturated delta-lactam was furnished by ring-closing metathesis. Although Baylis-Hillman chemistry failed on this cyclic compound, introduction of the hydroxyethyl group prior to ring-closing metathesis was successful. A Baylis-Hillman reaction was used to introduce the substituent at the alpha-position of the alpha,beta-unsaturated lactam. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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