Pd(II)/Bronsted Acid Catalyzed Enantioselective Allylic C-H Activation for the Synthesis of Spirocyclic Rings

被引：185

作者：

Chai, Zhuo ^{[1
]}

Rainey, Trevor J. ^{[1
]}

机构：

[1] Montana State Univ, Dept Chem & Biochem, Bozeman, MT 59717 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 08期

关键词：

BRONSTED ACID; TERMINAL ALKENES; PALLADIUM; OLEFINS; AMINATION; METAL; ACETOXYLATION; OXIDATION; CONSTRUCTION; EXPANSION;

D O I：

10.1021/ja2102407

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Pd(II)/Bronsted acid catalyzed migratory ring expansion for the synthesis of indene derivatives possessing a stereogenic spirocyclic carbon center was developed. This transformation is believed to mechanistically proceed via enantioselective allylic C-H activation with concomitant semipinacol ring expansion to the nascent pi-allylpalladium species. Enantioselectivities as high as 98% ee were attainable.

引用

页码：3615 / 3618

页数：4

共 61 条

[1]

Albel U., 2006, BIOORG MED CHEM LETT, V16, P3292

[2] ASYMMETRIC-SYNTHESIS OF ACIDS BY THE PALLADIUM-CATALYZED HYDROCARBOXYLATION OF OLEFINS IN THE PRESENCE OF (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIYL OR (S)-(+)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGEN PHOSPHATE [J].

ALPER, H ;

HAMEL, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) :2803-2804

[3] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[4] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].

Boele, MDK ;

van Strijdonck, GPF ;

de Vries, AHM ;

Kamer, PCJ ;

de Vries, JG ;

van Leeuwen, PWNM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587

[5] Allylic C-H Acetoxylation with a 4,5-Diazafluorenone-Ligated Palladium Catalyst: A Ligand-Based Strategy To Achieve Aerobic Catalytic Turnover [J].

Campbell, Alison N. ;

White, Paul B. ;

Guzei, Ilia A. ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15116-15119

[6] Serial ligand catalysis: A highly selective allylic C-H oxidation [J].

Chen, MS ;

Prabagaran, N ;

Labenz, NA ;

White, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6970-6971

[7] A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation [J].

Chen, MS ;

White, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) :1346-1347

[8] A Bronsted acid catalyst for the enantioselective protonation reaction [J].

Cheon, Cheol Hong ;

Yamamoto, Hisashi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9246-+

[9] Stereoselective construction of quaternary stereocenters [J].

Christoffers, J ;

Baro, A .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1473-1482

[10] Kinetic Resolution of Homoaldols via Catalytic Asymmetric Transacetalization [J].

Coric, Ilija ;

Mueller, Steffen ;

List, Benjamin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (49) :17370-17373

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