Preparation of Chiral 3-Arylpyrrolidines via the Enantioselective 1,4-Addition of Arylboronic Acids to Fumaric Esters Catalyzed by Rh(I)/Chiral Diene Complexes

被引：37

作者：

Chung, Yu-Chiang ^{[1
]}

Janmanchi, Damodar ^{[1
]}

Wu, Hsyueh-Liang ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 11677, Taiwan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 11期

关键词：

ASYMMETRIC 1,4-ADDITION; CONJUGATE ADDITIONS; LIGANDS; LIGNANS;

D O I：

10.1021/ol300980k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylboronic acids to di-fert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94 -> 99.5% ee. Excellent enantioselectivities were also observed in the regio- and enantioselective conjugate addition of phenylboronic acid (4a) to compound 3e.

引用

页码：2766 / 2769

页数：4

共 32 条

[1]

Agami C, 2002, EUR J ORG CHEM, V2002, P29, DOI 10.1002/1099-0690(20021)2002:1<29::AID-EJOC29>3.0.CO

[2]

2-B

[3]

[Anonymous], [No title captured]

[4]

Ayres D.C., 1990, LIGNANS CHEM BIOL CL

[5] All-carbon quaternary stereogenic centers by enantioselective Cu-catalyzed conjugate additions promoted by a chiral N-heterocyclic carbene [J].

Brown, M. Kevin ;

May, Tricia L. ;

Baxter, Carl A. ;

Hoveyda, Amir H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1097-1100

[6] Chiral olefins as steering ligands in asymmetric catalysis [J].

Defieber, Christian ;

Gruetzmacher, Hansjoerg ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) :4482-4502

[7] Readily available [2.2.2]-bicyclooctadienes as new chiral ligands for Ir(I): Catalytic, kinetic resolution of allyl carbonates [J].

Fischer, C ;

Defieber, C ;

Suzuki, T ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1628-1629

[8] C1-symmetric monosubstituted chiral diene ligands in asymmetric rhodium-catalyzed 1,4-addition reactions [J].

Gendrineau, Thomas ;

Chuzel, Olivier ;

Eijsberg, Hendrik ;

Genet, Jean-Pierre ;

Darses, Sylvain .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (40) :7669-7672

[9] Room-Temperature Rhodium-Catalyzed Asymmetric 1,4-Addition of Potassium Trifluoro(organo)borates [J].

Gendrineau, Thomas ;

Genet, Jean-Pierre ;

Darses, Sylvain .

ORGANIC LETTERS, 2009, 11 (15) :3486-3489

[10] Chiral olefin Ligands - New "Spectators" in asymmetric catalysis [J].

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3364-3366

← 1 2 3 4 →