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铑催化的β,γ-不饱和α-酮酯的不对称共轭炔基化反应。

Rhodium-Catalyzed Asymmetric Conjugate Alkynylation of β,γ-Unsaturated α-Ketoesters.

机构信息

Department of Organic Chemistry and ‡State Key Laboratory of Natural Medicines, China Pharmaceutical University , 24 Tongjiaxiang, Nanjing 210009, China.

出版信息

Org Lett. 2017 May 5;19(9):2378-2381. doi: 10.1021/acs.orglett.7b00909. Epub 2017 Apr 27.

Abstract

The first example of catalytic asymmetric conjugate alkynylation of β,γ-unsaturated α-ketoesters is reported. By using Rh(I)/(R)-DM-binap complex as the catalyst and diphenyl[(triisopropylsilyl)ethynyl]methanol as the alkynylating reagent, the alkynylation reaction proceeded smoothly to afford α-ketoesters bearing a propargylic chiral center at γ position in good yields with high enantioselectivities.

摘要

首次报道了β,γ-不饱和α-酮酯的催化不对称共轭炔基化反应。使用 Rh(I)/(R)-DM-binap 配合物作为催化剂,二苯[(三异丙基硅基)乙炔基]甲醇作为炔基化试剂,该炔基化反应能够顺利进行,以高产率和高对映选择性得到在γ位带有炔丙基手性中心的α-酮酯。

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