Selective Synthesis of Six Products from a Single Indolyl α-Diazocarbonyl Precursor

被引：57

作者：

James, Michael J. ^{[1
]}

Brien, Peter O. I. ^{[1
]}

Taylor, Richard J. K. ^{[1
]}

Unsworth, William P. ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 33期

关键词：

cyclizations; diazo compounds; indoles; spirocycles; synthetic methods; C-H FUNCTIONALIZATION; SPIROCYCLIC INDOLENINES; ALLYLIC DEAROMATIZATION; MEDICINAL CHEMISTS; SCAFFOLDS; CARBAZOLES; DIVERSE; COPPER; ACIDS; DIAZOKETONES;

D O I：

10.1002/anie.201605337

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Indolyl alpha-diazocarbonyls can be selectively cyclized to give six distinct products through the careful choice of catalyst and reaction conditions. A range of catalysts were used, including complexes of Rh-II, Pd-II, and C-uII, as well as SiO2, to promote diazo decomposition and subsequent cyclization/rearrangement through a range of mechanistic pathways.

引用

页码：9671 / 9675

页数：5

共 48 条

[1]

[Anonymous], 14819244A CCDC

[2]

[Anonymous], 2012, ANGEW CHE

[3] 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

[4] From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis [J].

Chambers, Sarah J. ;

Coulthard, Graeme ;

Unsworth, William P. ;

O'Brien, Peter ;

Taylor, Richard J. K. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (19) :6496-6500

[5] Copper-Catalyzed Divergent Addition Reactions of Enoldiazoacetamides with Nitrones [J].

Cheng, Qing-Qing ;

Yedoyan, Julietta ;

Arman, Hadi ;

Doyle, Michael P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) :44-47

[6]

Cooper T. W. J., 2010, ANGEW CHEM, V122, P8258

[7] Factors Determining the Selection of Organic Reactions by Medicinal Chemists and the Use of These Reactions in Arrays (Small Focused Libraries) [J].

Cooper, Tony W. J. ;

Campbell, Ian B. ;

Macdonald, Simon J. F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) :8082-8091

[8] Rhodium(II) catalyzed intramolecular insertion of carbenoids derived from 2-pyrrolyl and 3-indolyl α-diazo-β-ketoesters and α-diazoketones [J].

Cuevas-Yañez, E ;

Muchowski, JM ;

Cruz-Almanza, R .

TETRAHEDRON, 2004, 60 (07) :1505-1511

[9] A novel approach to the efficient oxygenation of hydrocarbons under mild conditions. Superior oxo transfer selectivity using dioxiranes [J].

Curci, R ;

D'Accolti, L ;

Fusco, C .

ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (01) :1-9

[10] Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion [J].

Davies, HML ;

Beckwith, REJ .

CHEMICAL REVIEWS, 2003, 103 (08) :2861-2903

← 1 2 3 4 5 →