Highly Enantioselective Pictet-Spengler Reactions with α-Ketoamide-Derived Ketimines: Access to an Unusual Class of Quaternary α-Amino Amides

被引：69

作者：

Bou-Hamdan, Farhan R. ^{[1
]}

Leighton, James L. ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 13期

基金：

美国国家科学基金会;

关键词：

asymmetric synthesis; heterocycles; ketimines; Lewis acids; Pictet-Spengler reaction; CHIRAL AUXILIARY GROUPS; SILICON LEWIS-ACID; ALLYLATION; DERIVATIVES; BENZOYLHYDRAZONES; ALDIMINES; REAGENT; ESTERS; ETHER; IONS;

D O I：

10.1002/anie.200806110

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Quat's" the story? N-Aryl amides are effective directing/activating groups for chlorosilane Lewis acids. This aspect has been exploited for the development of the first simple and general method for the highly enantioselective Pictet-Spengler reaction of ketimines derived from α-ketoamides leading to quaternary α-amino acid derivatives (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA."

引用

页码：2403 / 2406

页数：4

共 35 条

[1]

AMANN R, 1991, ANGEW CHEM INT EDIT, V30, P1320, DOI 10.1002/anie.199113201

[2]

AMANN R, 1991, ANGEW CHEM, V103, P1373

[3] Enantioselective allylation of ketone-derived benzoylhydrazones: Practical synthesis of tertiary carbinarnines [J].

Berger, R ;

Duff, K ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5686-5687

[4] Toward a versatile allylation reagent: Practical, enantioselective allylation of acylhydrazones using strained silacycles [J].

Berger, R ;

Rabbat, PMA ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9596-9597

[5]

BOHLMANN C, 1985, LIEBIGS ANN CHEM, P1752

[6] ASYMMETRIC PICTET-SPENGLER SYNTHESIS OF TETRAHYDROISOQUINOLINES - AN ENANTIOSELECTIVE SYNTHESIS OF (-)-LAUDANOSINE [J].

COMINS, DL ;

BADAWI, MM .

TETRAHEDRON LETTERS, 1991, 32 (26) :2995-2996

[7] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

[8] Strategies for the synthesis of novel indole alkaloid-based screening libraries for drug discovery [J].

Fokas, Demosthenes ;

Yu, Libing ;

Baldino, Carmen M. .

MOLECULAR DIVERSITY, 2005, 9 (1-3) :81-89

[9]

Huber J. D., 2008, ANGEW CHEM, V120, P3079

[10] Allylsilane-vinylarene cross-metathesis enables a powerful approach to enantioselective imine allylation [J].

Huber, John D. ;

Perl, Nicholas R. ;

Leighton, James L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) :3037-3039

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