Readily available biaryl P,N ligands for asymmetric catalysis

被引：317

作者：

Knöpfel, TF ^{[1
]}

Aschwanden, P ^{[1
]}

Ichikawa, T ^{[1
]}

Watanabe, T ^{[1
]}

Carreira, EM ^{[1
]}

机构：

[1] ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 44期

关键词：

asymmetric catalysis; atropisomerism; heterocycles; hydroboration; P; N ligands;

D O I：

10.1002/anie.200461286

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A short and modular synthesis of novel P,N ligands (pinap; see scheme; X = O or NH) is presented. A covalently bound chiral group allows the separation of the atropisomeric diastereomers, thus avoiding resolution involving chiral Pd-amine complexes. The utility of the ligands is demonstrated for three reactions catalyzed by different transition metals; in each case products are obtained with high enantiomeric excess (up to 99% ee).

引用

页码：5971 / 5973

页数：3

共 25 条

[1] ALOCK NW, 1993, TETRAHEDRON-ASYMMETR, V4, P743
[2] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes
Anand, NK
Carreira, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) : 9687 - 9688
[3] ENAMINE CHEMISTRY .1. REACTIONS WITH NONACTIVATED TERMINAL ACETYLENIC COMPOUNDS
BRANNOCK, KC
BURPITT, RD
THWEATT, JG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) : 1462 - &
[4] EFFECTIVE ASYMMETRIC HYDROBORATION CATALYZED BY A RHODIUM COMPLEX OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE
BROWN, JM
HULMES, DI
LAYZELL, TP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (22) : 1673 - 1674
[5] Chiral P,N-ligands with pyridine-nitrogen and phosphorus donor atoms.: Syntheses and applications in asymmetric catalysis
Chelucci, G
Orrù, G
Pinna, GA
[J]. TETRAHEDRON, 2003, 59 (48) : 9471 - 9515
[6] Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis
Chen, C
Li, XD
Schreiber, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) : 10174 - 10175
[7] Doucet H, 1999, CHEM-EUR J, V5, P1320, DOI 10.1002/(SICI)1521-3765(19990401)5:4<1320::AID-CHEM1320>3.0.CO
[8] 2-#
[9] A new chiral at metal catalyst for enantioselective Diels-Alder reactions: Observation of isomeric intermediates
Faller, JW
Grimmond, BJ
[J]. ORGANOMETALLICS, 2001, 20 (12) : 2454 - 2458
[10] Direct addition of TMS-acetylene to aldimines catalyzed by a simple, commercially available Ir(I) complex
Fischer, C
Carreira, EM
[J]. ORGANIC LETTERS, 2001, 3 (26) : 4319 - 4321

← 1 2 3 →