Organocatalytic enantioselective indole alkylations of α,β-unsaturated ketones

被引：144

作者：

Chen, Wei

Du, Wei

Yue, Lei

Li, Rui

Wu, Yong

Ding, Li-Sheng

Chen, Ying-Chun ^{[1
]}

机构：

[1] Sichuan Univ, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Peoples R China

[2] Sichuan Univ, W China Sch Pharm, Dept Med Chem, Chengdu 610041, Peoples R China

[3] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

[4] Sichuan Univ, W China Hosp, State Key Lab Biotherapy, Chengdu 610064, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2007年 / 5卷 / 05期

关键词：

D O I：

10.1039/b616504d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C3-selective enantioselective Michael-type Friedel - Crafts alkylations of indoles with nonchelating alpha, beta-unsaturated alkyl ketones, catalysed by a chiral primary amine derived from natural cinchonine, were investigated. The reactions, in the presence of 30 mol% catalyst, were smoothly conducted at 0 to - 20 degrees C. Moderate to good ee ( 47 - 89%) has been achieved.

引用

页码：816 / 821

页数：6

共 45 条

[1] Preparation of enantiopure 6-(3-indolyl)-2-piperidones and conjugate additions to a 3,4-didehydro derivative
Amat, M
Llor, N
Bosch, J
Solans, X
[J]. TETRAHEDRON, 1997, 53 (02) : 719 - 730
[2] [Anonymous], ACC CHEM RES
[3] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B
Austin, JF
Kim, SG
Sinz, CJ
Xiao, WJ
MacMillan, DWC
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5482 - 5487
[4] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis
Austin, JF
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1172 - 1173
[5] A journey across recent advances in catalytic and stereoselective alkylation of indoles
Bandini, M
Melloni, A
Tommasi, S
Umani-Ronchi, A
[J]. SYNLETT, 2005, (08) : 1199 - 1222
[6] Can simple enones be useful partners for the catalytic stereoselective alkylation of indoles?
Bandini, M
Fagioli, M
Garavelli, M
Melloni, A
Trigari, V
Umani-Ronchi, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) : 7511 - 7518
[7] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction
Bandini, M
Melloni, A
Umani-Ronchi, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) : 550 - 556
[8] Catalytic enantioselective conjugate addition of indoles to simple α,β-unsaturated ketones
Bandini, M
Fagioli, M
Melchiorre, P
Melloni, A
Umani-Ronchi, A
[J]. TETRAHEDRON LETTERS, 2003, 44 (31) : 5843 - 5846
[9] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[10] ENANTIOSELECTIVE CATALYSIS .98. PREPARATION OF 9-AMINO(9-DEOXY)CINCHONA ALKALOIDS
BRUNNER, H
BUGLER, J
NUBER, B
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1699 - 1702

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