Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations

被引：320

作者：

Bhat, Vikram ^{[1
]}

Welin, Eric R. ^{[2
]}

Guo, Xuelei ^{[1
]}

Stoltz, Brian M. ^{[2
]}

机构：

[1] AbbVie Inc, Pasadena, CA 91125 USA

[2] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

CHEMICAL REVIEWS | 2017年 / 117卷 / 05期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; SECONDARY ALKYL ELECTROPHILES; DECARBOXYLATIVE ALLYLIC ALKYLATION; INTRAMOLECULAR HECK REACTIONS; NEGISHI CROSS-COUPLINGS; QUATERNARY CARBON CENTERS; BETA-ARYLOXY ALCOHOLS; ALPHA-KETO ESTERS; C-H ACTIVATION; TRANSFER HYDROGENATION;

D O I：

10.1021/acs.chemrev.6b00731

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stereoconvergent catalysis is an important subset of asymmetric synthesis that encompasses stereoablative transformations, dynamic kinetic resolutions, and dynamic kinetic asymmetric transformations. Initially, only enzymes were known to catalyze dynamic kinetic processes, but recently various synthetic catalysts have been developed. This Review summarizes major advances in nonenzymatic, transition-metal-promoted dynamic asymmetric transformations reported between 2005 and 2015.

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页码：4528 / 4561

页数：34

相关论文

共 254 条

[1] SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES [J].

ACHMATOWICZ, O ;

BUKOWSKI, P ;

SZECHNER, B ;

ZWIERZCHOWSKA, Z ;

ZAMOJSKI, A .

TETRAHEDRON, 1971, 27 (10) :1973-+

[2] TOTAL SYNTHESIS OF MONOSACCHARIDES - SYNTHESIS OF METHYL DL-PENTOPYRANOSIDES WITH ALPHA AND BETA-LYXO, BETA-RIBO, ALPHA-XYLO, AND ALPHA-ARABINO CONFIGURATIONS FROM FURFURYL ALCOHOL [J].

ACHMATOWICZ, O ;

BUKOWSKI, P .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (17) :2524-2529

[3] Multimetallic catalysed cross-coupling of aryl bromides with aryl triflates [J].

Ackerman, Laura K. G. ;

Lovell, Matthew M. ;

Weix, Daniel J. .

NATURE, 2015, 524 (7566) :454-+

[4] Highly Enantioselective Control of Dynamic Cascade Transformations by Dual Catalysis: Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles [J].

Afewerki, Samson ;

Ma, Guangning ;

Ibrahem, Ismail ;

Liu, Leifeng ;

Sun, Junliang ;

Cordova, Armando .

ACS CATALYSIS, 2015, 5 (02) :1266-1272

[5] Racemization catalysts for the dynamic kinetic resolution of alcohols and amines [J].

Ahn, Yangsoo ;

Ko, Soo-Byung ;

Kim, Mahn-Joo ;

Park, Jaiwook .

COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :647-658

[6] General asymmetric hydrogenation of α-branched aromatic ketones catalyzed by TolBINAP/DMAPEN-ruthenium(II) complex [J].

Arai, Noriyoshi ;

Ooka, Hirohito ;

Azuma, Keita ;

Yabuuchi, Toshio ;

Kurono, Nobuhito ;

Inoue, Tsutomu ;

Ohkuma, Takeshi .

ORGANIC LETTERS, 2007, 9 (05) :939-941

[7] Rhodium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Racemic Tertiary Allylic Trichloroacetimidates with Anilines [J].

Arnold, Jeffrey S. ;

Nguyen, Hien M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (20) :8380-8383

[8] Rhodium-Catalyzed Regioselective Amination of Secondary Allylic Trichloroacetimidates with Unactivated Aromatic Amines [J].

Arnold, Jeffrey S. ;

Stone, Robert F. ;

Nguyen, Hien M. .

ORGANIC LETTERS, 2010, 12 (20) :4580-4583

[9] Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides [J].

Arp, FO ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) :10482-10483

[10] CATALYTIC ASYMMETRIC-SYNTHESIS OF EITHER ENANTIOMER OF PHYSOSTIGMINE - FORMATION OF QUATERNARY CARBON CENTERS WITH HIGH ENANTIOSELECTION BY INTRAMOLECULAR HECK REACTIONS OF (Z)-2-BUTENANILIDES [J].

ASHIMORI, A ;

MATSUURA, T ;

OVERMAN, LE ;

POON, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6949-6951

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