Asymmetric catalysis mediated by synthetic peptides

被引：518

作者：

Davie, Elizabeth A. Colby ^{[1
,2
,3
]}

Mennen, Steven M. ^{[2
]}

Xu, Yingju ^{[2
]}

Miller, Scott J. ^{[1
,2
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

[2] Boston Coll, Dept Chem, Chestnut Hill, MA 02467 USA

[3] Assumption Coll, Worcester, MA 01609 USA

来源：

CHEMICAL REVIEWS | 2007年 / 107卷 / 12期

关键词：

D O I：

10.1021/cr068377w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Recent works in the arena of group transfer reactions, enantioselective protonation of enolates, Michael additions and the Morita-Baylis-Hillman reaction have firmly established small peptides as versatile, enantioselective catalysts. The review also covered enantioselective oxidative and reductive methods; enantioselective protonation; enantioselective conjugate addition of azide; peptide-catalyzed hydrolysis of esters; peptide-catalyzed asymmetric acylation; phosphorylation; and sulfinyl transfer.

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收藏

页码：5759 / 5812

页数：54

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共 297 条

[1] ELECTROORGANIC REACTIONS ON ORGANIC ELECTRODES .5. STEREOCHEMICAL STUDIES OF THE ELECT REACTIONS OF ORGANIC-COMPOUNDS .24. DURABLE CHIRAL GRAPHITE-ELECTRODES MODIFIED CHEMICALLY WITH POLY(L-VALINE) AND POLY(N-ACRYLOYL-L-VALINE METHYL-ESTER) [J].

ABE, S ;

NONAKA, T .

CHEMISTRY LETTERS, 1983, (10) :1541-1542

[2] ELECTROORGANIC REACTIONS ON ORGANIC ELECTRODES .4. STEREOCHEMICAL STUDIES OF THE ELECTROLYTIC REACTIONS OF ORGANIC-COMPOUNDS .23. ELECTROCHEMICAL ASYMMETRIC REDUCTION OF PROCHIRAL CARBONYL-COMPOUNDS, OXIMES, AND A GEM-DIHALIDE ON A POLY-L-VALINE-COATED GRAPHITE ELECTRODE [J].

ABE, S ;

FUCHIGAMI, T ;

NONAKA, T .

CHEMISTRY LETTERS, 1983, (07) :1033-1036

[3] STEREOCHEMICAL STUDIES OF THE ELECTROLYTIC REACTIONS OF ORGANIC-COMPOUNDS .19. ELECTROORGANIC REACTIONS ON ORGANIC ELECTRODES .1. ASYMMETRIC REDUCTION OF PROCHIRAL ACTIVATED OLEFINS ON A POLY-L-VALINE-COATED GRAPHITE [J].

ABE, S ;

NONAKA, T ;

FUCHIGAMI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) :3630-3632

[4] Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones:: total synthesis of diltiazem and Taxol™ side-chain [J].

Adger, BM ;

Barkley, JV ;

Bergeron, S ;

Cappi, MW ;

Flowerdew, BE ;

Jackson, MP ;

McCague, R ;

Nugent, TC ;

Roberts, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (23) :3501-3507

[5] Direct asymmetric aldol reaction in aqueous media using polymer-supported peptide [J].

Akagawa, K ;

Sakamoto, S ;

Kudo, K .

TETRAHEDRON LETTERS, 2005, 46 (47) :8185-8187

[6] Polyamino acid-catalysed asymmetric epoxidation: Sodium percarbonate as a source of base and oxidant [J].

Allen, JV ;

Drauz, KH ;

Flood, RW ;

Roberts, SM ;

Skidmore, J .

TETRAHEDRON LETTERS, 1999, 40 (29) :5417-5420

[7] Julia-Colonna asymmetric epoxidation reactions under non-aqueous conditions: Rapid, highly regio- and stereo-selective transformations using a cheap, recyclable catalyst [J].

Allen, JV ;

Bergeron, S ;

Griffiths, MJ ;

Mukherjee, S ;

Roberts, SM ;

Williamson, NM ;

Wu, LE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (19) :3171-3179

[8] Stereoselective epoxidation of electron poor dienes using poly(L-leucine) [J].

Allen, JV ;

Cappi, MW ;

Kary, PD ;

Roberts, SM ;

Williamson, NM ;

Wu, LE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (22) :3297-3298

[9] Heterogeneous catalysis of the asymmetric aldol reaction by solid-supported proline-terminated peptides [J].

Andreae, MRM ;

Davis, AP .

TETRAHEDRON-ASYMMETRY, 2005, 16 (14) :2487-2492

[10] Dihedral angle restriction within a peptide-based tertiary alcohol kinetic resolution catalyst [J].

Angione, Mary C. ;

Miller, Scott J. .

TETRAHEDRON, 2006, 62 (22) :5254-5261

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