Catalytic asymmetric addition of alcohols to imines:: Enantioselective preparation of chiral N,O-aminals

被引：160

作者：

Li, Guilong ^{[1
]}

Fronczek, Frank R. ^{[2
]}

Antilla, Jon C. ^{[1
]}

机构：

[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA

[2] Louisiana State Univ, Dept Chem, Xray Lab, Baton Rouge, LA 70803 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 37期

关键词：

D O I：

10.1021/ja8033334

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective addition of alcohols to imine electrophiles has been shown to proceed in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction allows for the formation of the respective chiral N,O-aminals in excellent yield and enantioselectivity. A total of 11 different alcohols and 11 different imines were successfully used as a clear demonstration of the reaction generality.

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页码：12216 / +

页数：3

相关论文

共 34 条

[1] 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

[2] Stronger bronsted acids [J].

Akiyama, Takahiko .

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

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

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

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

[4] Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: Control of stereochemistry via a chiral bronsted acid activated dipole [J].

Chen, Xiao-Hua ;

Zhang, Wen-Quan ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5652-+

[5] Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family [J].

Cichewicz, RH ;

Valeriote, FA ;

Crews, P .

ORGANIC LETTERS, 2004, 6 (12) :1951-1954

[6] Chiral phosphoric acids: Powerful organocatalysts for asymmetric addition reactions to imines [J].

Connon, Stephen J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3909-3912

[7]

Dalko P.I., 2007, ENANTIOSELECTIVE ORG

[8] The development of double axially chiral phosphoric acids and their catalytic transfer hydrogenation of quinolines [J].

Guo, Qun-Sheng ;

Du, Da-Ming ;

Xu, Jiaxi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (04) :759-762

[9] Oxidative entry to α-oxy N-acyl aminals and hemiaminals:: efficient formation of 2-(N-acylaminal) substituted tetrahydropyrans [J].

Huang, Xianhai ;

Shao, Ning ;

Palani, Anandan ;

Aslanian, Robert .

TETRAHEDRON LETTERS, 2007, 48 (11) :1967-1971

[10] Total synthesis of pederin [J].

Jewett, John C. ;

Rawal, Viresh H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) :6502-6504

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