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铜催化的高对映选择性合成 ()-δ-乙烯基高烯丙醇。

Cu-Catalyzed Highly Stereoselective Syntheses of ()-δ-Vinyl-homoallylic Alcohols.

机构信息

Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849, United States.

College of Pharmacy, State Key Laboratory of Medical Chemical Biology, Nankai University, Tianjin, China.

出版信息

Org Lett. 2021 Aug 6;23(15):6035-6040. doi: 10.1021/acs.orglett.1c02086. Epub 2021 Jul 20.

Abstract

Stereoselective synthesis of ()-δ-vinyl-homoallylic alcohols was developed. Starting from α-vinyl allylboronate, Cu-catalyzed allylation of aldehydes or ketones forms secondary or tertiary δ-vinyl-homoallylic alcohols with high -selectivities. It is proposed that the reaction operates under the Curtin-Hammett principle via the intermediacy of α-vinyl allylic copper species to give the alcohol products with high -selectivities.

摘要

发展了()-δ-乙烯基高烯丙醇的立体选择性合成。以α-乙烯基烯丙基硼酸酯为起始原料,Cu 催化醛或酮的烯丙基化反应,以高立体选择性得到仲或叔δ-乙烯基高烯丙醇。该反应遵循 Curtin-Hammett 原理,经由α-乙烯基烯丙基铜物种中间体进行,得到高立体选择性的醇产物。

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