Asymmetric construction of quaternary carbon stereocenter by Pd-catalyzed intramolecular α-arylation

被引：30

作者：

Arao, Takafumi ^{[1
]}

Kondo, Kazuhiro ^{[1
]}

Aoyama, Toyohiko ^{[1
]}

机构：

[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2006年 / 54卷 / 12期

关键词：

enantioselective intramolecular alpha-arylation; quaternary carbon; H-8-BINAP; chiral N-heterocyclic carbene;

D O I：

10.1248/cpb.54.1743

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The catalyst comprised of Pd(OAc)(2) and H-8-BINAP provides good reaction conversions for a catalytic enantioselective intramolecular alpha-arylation of N-(2-bromophenyl)-N-methyl-2-arylpropanamide to form the quaternary carbon with up to 68% enantioselectivity.

引用

页码：1743 / 1747

页数：5

共 21 条

[1] Development of an N-heterocyclic carbene ligand based on concept of chiral mimetic
Arao, T
Kondo, K
Aoyama, T
[J]. TETRAHEDRON LETTERS, 2006, 47 (09) : 1417 - 1420
[2] ARAO T, 2006, IN PRESS SYNTHEIS
[3] Function of an N-heterocyclic carbene ligand based on concept of chiral mimetic
Arao, Takafumi
Sato, Kei
Kondo, Kazuhiro
Aoyama, Toyohiko
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (11) : 1576 - 1581
[4] Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[5] 2-V
[6] Catalytic asymmetric synthesis of all-carbon quaternary stereocenters
Douglas, CJ
Overman, LE
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5363 - 5367
[7] Oxazolines as chiral building blocks for imidazolium salts and N-heterocyclic carbene ligands
Glorius, F
Altenhoff, G
Goddard, R
Lehmann, C
[J]. CHEMICAL COMMUNICATIONS, 2002, (22) : 2704 - +
[8] Palladium-catalyzed direct α-arylation of ketones.: Rate acceleration by sterically hindered chelating ligands and reductive elimination from a transition metal enolate complex
Hamann, BC
Hartwig, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12382 - 12383
[9] Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions
Hayashi, T
Yamasaki, K
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2829 - 2844
[10] Asymmetric Kumada-Corriu cross-coupling reaction with Pd2(dba)3 and an N-Ar axially chiral mimetic-type ligand catalyst
Hideo, H
Fukuda, Y
Kondo, K
Okuno, H
Murakami, Y
Aoyama, T
[J]. TETRAHEDRON, 2004, 60 (47) : 10701 - 10709

← 1 2 3 →