The state of the art in asymmetric induction: the aldol reaction as a case study

被引：193

作者：

Geary, Laina M. ^{[1
]}

Hultin, Philip G. ^{[1
]}

机构：

[1] Univ Manitoba, Dept Chem, Winnipeg, MB R3T 2N2, Canada

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 02期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ENANTIOSELECTIVE MUKAIYAMA-ALDOL; LEWIS-BASE ACTIVATION; TITANIUM-CARBOHYDRATE COMPLEXES; HIGHLY STEREOSELECTIVE ORGANOCATALYST; BIS(OXAZOLINE) COPPER(II) COMPLEXES; SCHOLLKOPF CHIRAL AUXILIARIES; PROTONIC ACID CATALYSTS; SMALL ORGANIC-MOLECULES; SILYL KETENE ACETALS; ACYCLIC AMINO-ACIDS;

D O I：

10.1016/j.tetasy.2008.12.030

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

This review highlights the achievements in asymmetric induction in the context of the aldol reaction during the years 2003-2007. While chiral auxiliary-mediated methods are the best understood and developed, catalytic methods based on chiral metal-ligand complexes and more recently organocatalysts promise to improve the efficacy and economics of asymmetric induction. This review provides a brief summary of work prior to 2003 on chiral auxiliaries, metal catalysts and organocatalysts, and then delineates the state of the art in each process. It appears that no one method of achieving asymmetric induction in the aldol reaction is universally Superior. (C) 2009 Published by Elsevier Ltd.

引用

页码：131 / 173

页数：43

共 451 条

[1] Boron-mediated aldol reaction of carboxylic esters [J].

Abiko, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (06) :387-395

[2] Mechanism of the double aldol reaction: The first spectroscopic characterization of a carbon-bound boron enolate derived from carboxylic esters [J].

Abiko, A ;

Inoue, T ;

Masamune, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (36) :10759-10764

[3] Boron-mediated double aldol reaction of carboxylic esters [J].

Abiko, A ;

Liu, JF ;

Buske, DC ;

Moriyama, S ;

Masamune, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) :7168-7169

[4] The first doubly borylated enolate as an intermediate of the double aldol reaction [J].

Abiko, A ;

Inoue, T ;

Furuno, H ;

Schwalbe, H ;

Fieres, C ;

Masamune, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4605-4606

[5] The anti-selective boron-mediated asymmetric aldol reaction of carboxylic esters [J].

Abiko, A ;

Liu, JF ;

Masamune, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (10) :2586-2587

[6] Domino hydroformylation/enantioselective cross-aldol addition [J].

Abillard, Olivier ;

Breit, Bernhard .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) :1891-1895

[7] Chiral-auxiliary-controlled diastereoselective epoxidations [J].

Adam, W ;

Zhang, AM .

SYNLETT, 2005, (07) :1047-1072

[8]

Agami C., 1988, B SOC CHIM FR, V3, P499

[9] A chiral Ag-based catalyst for practical, efficient, and highly enantioselective additions of enolsilanes to α-ketoesters [J].

Akullian, Laura C. ;

Snapper, Marc L. ;

Hoveyda, Amir H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (20) :6532-6533

[10] The direct catalytic asymmetric cross-aldol reaction of aldehydes [J].

Alcaide, B ;

Almendros, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (08) :858-860

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