Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity

被引：1425

作者：

Giri, Ramesh ^{[2
]}

Shi, Bing-Feng ^{[1
]}

Engle, Keary M. ^{[1
]}

Maugel, Nathan ^{[3
]}

Yu, Jin-Quan ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

[3] Brandeis Univ, Dept Chem, Waltham, MA 02453 USA

来源：

CHEMICAL SOCIETY REVIEWS | 2009年 / 38卷 / 11期

基金：

美国国家科学基金会;

关键词：

ASYMMETRIC ALLYLIC OXIDATION; CARBON-HYDROGEN INSERTION; MARINE NATURAL-PRODUCTS; CATIONIC IR(I) COMPLEX; BOND ACTIVATION; INTRAMOLECULAR ALKYLATION; COUPLING POLYMERIZATION; CHIRAL RUTHENIUM; OXOVANADIUM(IV) COMPLEXES; STEREOSELECTIVE-SYNTHESIS;

D O I：

10.1039/b816707a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This critical review discusses historical and contemporary research in the field of transition metal-catalyzed carbon-hydrogen (C-H) bond activation through the lens of stereoselectivity. Research concerning both diastereoselectivity and enantioselectivity in C-H activation processes is examined, and the application of concepts in this area for the development of novel carbon-carbon and carbon-heteroatom bond-forming reactions is described. Throughout this review, an emphasis is placed on reactions that are (or may soon become) relevant in the realm of organic synthesis (221 references).

引用

收藏

页码：3242 / 3272

页数：31

相关论文

共 228 条

[1] Copper catalyzed allylic oxidation with peresters [J].

Andrus, MB ;

Lashley, JC .

TETRAHEDRON, 2002, 58 (05) :845-866

[2] Highly enantioselective copper-bisoxazoline-catalyzed allylic oxidation of cyclic olefins with tert-butyl p-nitroperbenzoate [J].

Andrus, MB ;

Zhou, ZN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) :8806-8807

[3] THE ASYMMETRIC KHARASCH REACTION - CATALYTIC ENANTIOSELECTIVE ALLYLIC ACYLOXYLATION OF OLEFINS WITH CHIRAL COPPER(I) COMPLEXES AND TERT-BUTYL PERBENZOATE [J].

ANDRUS, MB ;

ARGADE, AB ;

CHEN, X ;

PAMMENT, MG .

TETRAHEDRON LETTERS, 1995, 36 (17) :2945-2948

[4] Catalytic enantioselective allylic oxidation of olefins with copper(I) catalysts and new perester oxidants [J].

Andrus, MB ;

Chen, X .

TETRAHEDRON, 1997, 53 (48) :16229-16240

[5] Efficient synthesis of 1,1′-binaphthyl and 2,2′-bi-o-tolyl-2,2′-bis(oxazoline)s and preliminary use for the catalytic asymmetric allylic oxidation of cyclohexene [J].

Andrus, MB ;

Asgari, D ;

Sclafani, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9365-9368

[6] Asymmetric allylic oxidation with biarylbisoxazoline-copper(I) catalysis [J].

Andrus, MB ;

Asgari, D .

TETRAHEDRON, 2000, 56 (32) :5775-5780

[7] Total synthesis of marine natural products without using protecting groups [J].

Baran, Phil S. ;

Maimone, Thomas J. ;

Richter, Jeremy M. .

NATURE, 2007, 446 (7134) :404-408

[8] A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole→dihydroindoloazocine cyclization [J].

Baran, PS ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7904-7905

[9] Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates [J].

Barhate, NB ;

Chen, CT .

ORGANIC LETTERS, 2002, 4 (15) :2529-2532

[10] Intramolecular regioselective insertion into unactivated prochiral carbon-hydrogen bonds with diazoacetates of primary alcohols catalyzed by chiral dirhodium(II) carboxamidates. Highly enantioselective total synthesis of natural lignan lactones [J].

Bode, JW ;

Doyle, MP ;

Protopopova, MN ;

Zhou, QL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9146-9155

← 1 2 3 4 5 6 7 8 9 10 →