Enantioselective Difunctionalization of Alkenes by a Palladium-Catalyzed Heck/Sonogashira Sequence

被引：105

作者：

Zhou, Lujia ^{[2
]}

Li, Sanliang ^{[1
]}

Xu, Bing ^{[2
]}

Ji, Danting ^{[2
]}

Wu, Lizuo ^{[3
]}

Liu, Yu ^{[3
]}

Zhang, Zhan-Ming ^{[1
]}

Zhang, Junliang ^{[1
,2
]}

机构：

[1] Fudan Univ, Dept Chem, 2005 Songhu Rd, Shanghai 200438, Peoples R China

[2] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

[3] Changchun Univ Technol, Adv Inst Mat Sci, Coll Chem & Life Sci, Changchun 130012, Jilin, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 07期

基金：

中国博士后科学基金;

关键词：

alkenes; alkynylation; asymmetric catalysis; palladium; quaternary stereocenters; PINACOL MACROCYCLIZATION CASCADE; SIGMA-BOND ACTIVATION; DIAZONAMIDE-A; UNACTIVATED OLEFINS; TERMINAL ALKYNES; HECK REACTION; DICARBOFUNCTIONALIZATION; CYCLIZATION; FUNCTIONALIZATION; CONSTRUCTION;

D O I：

10.1002/anie.201913367

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sonogashira-type cross-couplings are one of the most significant alkynylations in organic chemistry. One of the first palladium-catalyzed intramolecular Heck/Sonogashira reactions of alkenes with terminal alkynes is now reported. With this method, a variety of uniquely substituted chiral benzene-fused heterocycles bearing a propargyl-substituted all-carbon quaternary stereocenter were obtained in a straightforward, high-yielding, and highly stereoselective manner under mild conditions. Salient features of this process include the use of readily available substrates, high selectivities, a broad substrate scope as well as versatile product functionalizations.

引用

页码：2769 / 2775

页数：7

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