Diastereoselective sulfur ylide rearrangements from gold catalyzed oxidation of ynamides

被引：3
作者：
Priest, Joshua D. [1 ]
Male, Louise [1 ]
Davies, Paul W. [1 ]
机构：
[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
来源：
TETRAHEDRON | 2021年 / 78卷
基金：
英国工程与自然科学研究理事会;
关键词：
Sulfur ylide; Rearrangement; Gold carbenoid; Oxidation; Ynamide; DOYLE-KIRMSE REACTION; 2,3 SIGMATROPIC REARRANGEMENT; ALLYLIC SULFIDES; TERMINAL ALKYNES; SULFONIUM YLIDE; INTERMOLECULAR REACTIONS; SELECTIVE SYNTHESIS; EFFICIENT; 1,1-DIBROMO-1-ALKENES; FUNCTIONALIZATION;
D O I：
10.1016/j.tet.2020.131757
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The [2,3]-sigmatropic rearrangement of sulfonium ylides bearing substituted allyl groups creates two contiguous stereocentres. Low diastereoselectivity is typically observed from commonly used alpha-diazocarboxylic ester precursors. High diastereoselectivity was previously revealed in a gold-catalyzed multicomponent route into allyl sulfonium ylides by reaction of ynamide, oxidant and allyl sulfides. The effect of substrate modifications on the diastereoselectivity have been studied, with N-phenyl methanesulfonamide derived ynamides proving the most effective. This report includes an enhanced experimental procedure, and a demonstration that the gold-catalyzed process remains highly effective at -78 degrees C. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：12
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