Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds

被引：148

作者：

Shintani, R ^{[1
]}

Ueyama, K ^{[1
]}

Yamada, I ^{[1
]}

Hayashi, T ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 19期

关键词：

D O I：

10.1021/ol048421z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds has been developed. While phosphorus-based chiral ligands fail to induce high stereoselectivity, chiral norbornadiene ligands have proved to be uniquely effective to achieve high enantioselectivity in these 1,4-addition reactions.

引用

页码：3425 / 3427

页数：3

共 50 条

[21] Chiral Bicyclic Bridgehead Phosphoramidite (Briphos) Ligands for Asymmetric Rhodium-Catalyzed 1,2-and 1,4-Addition
Lee, Ansoo
Kim, Hyunwoo
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09): : 3520 - 3527
[22] C1-symmetric monosubstituted chiral diene ligands in asymmetric rhodium-catalyzed 1,4-addition reactions
Gendrineau, Thomas
Chuzel, Olivier
Eijsberg, Hendrik
Genet, Jean-Pierre
Darses, Sylvain
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (40) : 7669 - 7672
[23] Rhodium-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to enones
Takaya, Y
Ogasawara, M
Hayashi, T
Sakai, M
Miyaura, N
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) : 5579 - 5580
[24] Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Indolylnitroalkenes
Xing, Junwei
Chen, Guihua
Cao, Peng
Liao, Jian
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (06) : 1230 - 1236
[25] Rhodium-catalyzed asymmetric 1,4-addition to 1-alkenylphosphonates
Hayashi, T
Senda, T
Takaya, Y
Ogasawara, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) : 11591 - 11592
[26] Synthesis of novel chiral phosphine-olefin complexes and their evaluation as ligands in the rhodium-catalyzed asymmetric 1,4-addition
Stemmler, Rene T.
Bolm, Carsten
SYNLETT, 2007, (09) : 1365 - 1370
[27] Rhodium-catalyzed asymmetric 1,4-addition of α,β-unsaturated imino esters using chiral bicyclic bridgehead phosphoramidite ligands
Kim, Hyunwoo
Lee, Ansoo
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
[28] Rhodium-Catalyzed Asymmetric 1,4-Addition of α,β-Unsaturated Imino Esters Using Chiral Bicyclic Bridgehead Phosphoramidite Ligands
Lee, Ansoo
Kim, Hyunwoo
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (35) : 11250 - 11253
[29] Easily accessible chiral dicyclopentadiene ligands for rhodium-catalyzed enantioselective 1,4-addition reactions
Shao, Cheng
Yu, Hong-Jie
Feng, Chen-Guo
Wang, Rui
Lin, Guo-Qiang
TETRAHEDRON LETTERS, 2012, 53 (22) : 2733 - 2735
[30] Chiral amidomonophosphine-rhodium(I) catalyst for asymmetric 1,4-addition of arylboronic acids to cycloalkenones
Kuriyama, M
Tomioka, K
TETRAHEDRON LETTERS, 2001, 42 (05) : 921 - 923

← 1 2 3 4 5 →