In situ catalyst improvement in the proline-mediated α-amination of aldehydes

被引：101

作者：

Iwamura, H ^{[1
]}

Mathew, SP ^{[1
]}

Blackmond, DG ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 38期

关键词：

D O I：

10.1021/ja046258x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Kinetic investigations show that the proline-mediated α-amination of aldehydes exhibits autoinductive rate behavior and amplification of product enantiomeric excess. Further experiments highlight the role of product, offering suggestions for the design of catalysts of improved efficiency for such transformations. The unusual characteristics exhibited by these reactions implicate amino acid catalysis in rationalizations of the origin of biological homochirality. Copyright © 2003 American Chemical Society.

引用

页码：11770 / 11771

页数：2

共 23 条

[1] Asymmetric autocatalysis and its implications for the origin of homochirality [J].

Blackmond, DG .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) :5732-5736

[2]

Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO

[3]

2-Y

[4] The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].

Brown, SP ;

Brochu, MP ;

Sinz, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809

[5] TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].

EDER, U ;

SAUER, G ;

WEICHERT, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&

[6] Nucleophilic chiral amines as catalysts in asymmetric synthesis [J].

France, S ;

Guerin, DJ ;

Miller, SJ ;

Lectka, T .

CHEMICAL REVIEWS, 2003, 103 (08) :2985-3012

[7] ON SPONTANEOUS ASYMMETRIC SYNTHESIS [J].

FRANK, FC .

BIOCHIMICA ET BIOPHYSICA ACTA, 1953, 11 (04) :459-463

[8] ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY [J].

HAJOS, ZG ;

PARRISH, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1615-1621

[9] Rational design of asymmetric organocatalysts - increased reactivity and solvent scope with a tetrazolic acid [J].

Hartikka, A ;

Arvidsson, PI .

TETRAHEDRON-ASYMMETRY, 2004, 15 (12) :1831-1834

[10] Amino acids and peptides as asymmetric organocatalysts [J].

Jarvo, ER ;

Miller, SJ .

TETRAHEDRON, 2002, 58 (13) :2481-2495

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