P,SLigands for the Asymmetric Construction of Quaternary Stereocenters in Palladium-Catalyzed Decarboxylative [4+2] Cycloadditions

被引：152

作者：

Wei, Yi ^{[1
]}

Lu, Liang-Qiu ^{[1
]}

Li, Tian-Ren ^{[1
]}

Feng, Bin ^{[1
]}

Wang, Qiang ^{[1
]}

Xiao, Wen-Jing ^{[1
]}

Alper, Howard ^{[1
]}

机构：

[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, CCNU uOttawa Joint Res Ctr, Minist Educ,Coll Chem, Wuhan 430079, Hubei, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 06期

关键词：

asymmetric catalysis; cycloaddition; heterocycles; ligand design; palladium; METHYLIDENE-DELTA-VALEROLACTONES; MIXED PHOSPHORUS/SULFUR LIGANDS; HYDROGENATION; DESIGN; BINOL;

D O I：

10.1002/anie.201509731

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new hybrid P,Sligand was exploited by combining a chiral -amino sulfide and a simple diphenyl phosphite. The resultant ligand performs extremely well in a palladium-catalyzed asymmetric decarboxylative [4+2] cycloaddition reaction, thus generating multiple contiguous stereocenters and a chiral quaternary center. By doing so, a straightforward route to highly functionalized tetrahydroquinolines was developed with yields of up to 99%, as well as 98% ee and greater than 95:5 d.r. Moreover, mechanistic insights into this transformation and the possible stereocontrol are discussed.

引用

页码：2200 / 2204

页数：5

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