Silver catalyzed proto- and sila-Nakamura-type α-vinylation of silyl enol ethers with dichloroacetylene. Divergent formation of stereochemically pure tri- and tetrasubstituted olefins

TETRAHEDRON LETTERS

卷:61

Article

Li, Lun^1,2  Wasik, Kimberly A.¹  Frost, Brian J.¹  Geary, Laina M.¹ 

[1] Univ Nevada, Dept Chem, Reno, NV 89557 USA

[2] Westlake Univ, Hangzhou, Peoples R China

关键词: Stereoselective;    Silver catalyzed;    Nakamura-type;    Vinylation;   

DOI  :  10.1016/j.tetlet.2019.151370

来源: Elsevier

【 摘 要 】

The silver-catalyzed reaction of silyl enol ethers with dichloroacetylene (DCA) is described. When DCA was used as a solution in diethyl ether, we found that the silyl group was transferred to the vinyl group, resulting in stereochemically pure tetrasubstituted olefins. However, when DCA was used as a solution in the more polar acetonitrile, protonation was the major pathway, and trisubstituted olefins were the dominant products. (C) 2019 Elsevier Ltd. All rights reserved.

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