Symmetry breaking in asymmetric catalysis: Racemic catalysis to autocatalysis

被引：186

作者：

Mikami, K ^{[1
]}

Yamanaka, M ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

来源：

CHEMICAL REVIEWS | 2003年 / 103卷 / 08期

关键词：

D O I：

10.1021/cr000260z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Recently, novel approaches for symmetry breaking in asymmetric catalysis were reported. Thus, the racemic catalysts can be enantiomer-selectively transformed into a highly activated enantiomeric catalyst by additional chiral sources. The nonequivalence of enantiomeric catalysts resulting from the spontaneous breaking of racemic catalysts was amplified by an asymmetric autocatalytic process. This paper discusses the recent progress in chirally economical racemic catalysis and followed by asymmetric amplification and autocatalysis.

引用

页码：3369 / 3400

页数：32

共 322 条

[1] RuHCl(diphosphine)(diamine): Catalyst precursors for the stereoselective hydrogenation of ketones and imines [J].

Abdur-Rashid, K ;

Lough, AJ ;

Morris, RH .

ORGANOMETALLICS, 2001, 20 (06) :1047-1049

[2] Ruthenium dihydride RuH2(PPh3)2((R,R)-cyclohexyldiamine) and ruthenium monohydride RuHCl(PPh3)2((R,R)-cyclohexyldiamine):: Active catalyst and catalyst precursor for the hydrogenation of ketones and imines [J].

Abdur-Rashid, K ;

Lough, AJ ;

Morris, RH .

ORGANOMETALLICS, 2000, 19 (14) :2655-2657

[3] Catalytic cycle for the asymmetric hydrogenation of prochiral ketones to chiral alcohols:: Direct hydride and proton transfer from chiral catalysts trans-Ru(H)2(diphosphine)(diamine) to ketones and direct addition of dihydrogen to the resulting hydridoamido complexes [J].

Abdur-Rashid, K ;

Faatz, M ;

Lough, AJ ;

Morris, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7473-7474

[4] GROWTH AND DISSOLUTION OF ORGANIC-CRYSTALS WITH TAILOR-MADE INHIBITORS - IMPLICATIONS IN STEREOCHEMISTRY AND MATERIALS SCIENCE [J].

ADDADI, L ;

BERKOVITCHYELLIN, Z ;

WEISSBUCH, I ;

VANMIL, J ;

SHIMON, LJW ;

LAHAV, M ;

LEISEROWITZ, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (06) :466-485

[5] THE ROLE OF THE PRODUCT IN ASYMMETRIC C-C BOND FORMATION - STOICHIOMETRIC AND CATALYTIC ENANTIOSELECTIVE AUTOINDUCTION [J].

ALBERTS, AH ;

WYNBERG, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (18) :7265-7266

[6] ENANTIOSELECTIVE AUTOINDUCTION IN THE ALDOL CONDENSATION OF ETHYL-ACETATE AND BENZALDEHYDE - SELECTIVE PRECIPITATION OF AN OPTICALLY INACTIVE LI-O-AGGREGATE [J].

ALBERTS, AH ;

WYNBERG, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) :453-454

[7] SUBSTRATE-INDUCED KINETIC RESOLUTION OF RACEMIC BIPHOSPHINES INSITU FOR HOMOGENEOUS CATALYSIS [J].

ALCOCK, NW ;

BROWN, JM ;

MADDOX, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (20) :1532-1534

[8]

Alexakis A, 2001, SYNLETT, P1375

[9] CHIRAL PHOSPHORUS LIGANDS FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS [J].

ALEXAKIS, A ;

FRUTOS, J ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2427-2430

[10]

Anastas P. T., 1998, GREEN CHEM THEORY PR

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