Asymmetric Bronsted acid catalyzed isoindoline synthesis: Enhancement of enantiomeric ratio by stereoablative kinetic resolution

被引：208

作者：

Enders, Dieter ^{[1
]}

Narine, Arun A. ^{[1
]}

Toulgoat, Fabien ^{[1
]}

Bisschops, Tom ^{[1
]}

机构：

[1] Univ Aachen, Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 30期

关键词：

asymmetric catalysis; aza-Michael addition; chiral Bronsted acids; Friedel-Crafts reaction; organocatalysis;

D O I：

10.1002/anie.200801354

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Improving with time: The first catalytic asymmetric synthesis of chiral 1,3-disubstituted isoindolines is based on a Brønsted acid catalyzed one-pot reaction consisting of a Friedel-Crafts reaction and a base-catalyzed aza-Michael addition (see scheme). The enantiomeric ratio of the product significantly increases with reaction time as a result of a Brønsted acid catalyzed stereoablative kinetic resolution, which occurs in tandem to the first step. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5661 / 5665

页数：5

共 80 条

[1] Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL [J].

Akiyama, T ;

Saitoh, Y ;

Morita, H ;

Fuchibe, K .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1523-1526

[2] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].

Akiyama, T ;

Morita, H ;

Itoh, J ;

Fuchibe, K .

ORGANIC LETTERS, 2005, 7 (13) :2583-2585

[3] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[4]

Akiyama T., 2004, ANGEW CHEM, V116, P1592, DOI DOI 10.1002/ANGE.200353240

[5] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[6] Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].

Akiyama, Takahiko ;

Morita, Hisashi ;

Fuchibe, Kohei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071

[7] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[8]

[Anonymous], 2006, ANGEW CHEM, V118, P1550

[9] A convenient method of synthesis of bis-indolylmethanes:: Indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases. [J].

Babu, G ;

Sridhar, N ;

Perumal, PT .

SYNTHETIC COMMUNICATIONS, 2000, 30 (09) :1609-1614

[10] Nucleophilic allylation-heterocyclization via bis-π-allylpalladium complexes:: Synthesis of five- and six-membered heterocycles [J].

Bao, M ;

Nakamura, H ;

Inoue, A ;

Yamamoto, Y .

CHEMISTRY LETTERS, 2002, (02) :158-159

← 1 2 3 4 5 6 7 8 →