Enantioselective double C-H activation of dihydronaphthalenes

被引：22

作者：

Davies, HML ^{[1
]}

Jin, QH ^{[1
]}

机构：

[1] SUNY Buffalo, Univ Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 12期

关键词：

D O I：

10.1021/ol050018k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dirhodium tetrakis((S)-N-(dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4)) catalyzed reaction of 1,2-dihydronaphthalenes with an excess of methyl vinyldiazoacetates results in a formal double C-H activation, generating four new stereogenic centers with very high stereoselectivity. The mechanism of the C-H activation is complex, involving a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement.

引用

页码：2293 / 2296

页数：4

共 20 条

[1] UNUSUALLY MILD AND SELECTIVE HYDROCARBON C-H BOND ACTIVATION WITH POSITIVELY CHARGED IRIDIUM(III) COMPLEXES [J].

ARNDTSEN, BA ;

BERGMAN, RG .

SCIENCE, 1995, 270 (5244) :1970-1973

[2] 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

[3] Catalytic asymmetric C-H activation of sp3 hybridized C-H bonds by means of carbenoid C-H insertions:: applications in organic synthesis [J].

Davies, HML .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 189 (01) :125-135

[4] Recent progress in asymmetric intermolecular C-H activation by rhodium carbenoid intermediates [J].

Davies, HML ;

Antoulinakis, EG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :47-55

[5] Direct synthesis of (+)-erogorgiaene through a kinetic enantiodifferentiating step [J].

Davies, HML ;

Walji, AM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1733-1735

[6] Highly diastereoselective and enantioselective C-H functionalization of 1,2-dihydronaphthalenes: A combined C-H activation/cope rearrangement followed by a retro-cope rearrangement [J].

Davies, HML ;

Jin, QH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (35) :10862-10863

[7] Double C-H activation strategy for the asymmetric synthesis of C2-Symmetric anilines [J].

Davies, HML ;

Jin, QH .

ORGANIC LETTERS, 2004, 6 (11) :1769-1772

[8] Catalytic asymmetric reactions for organic synthesis: The combined C-H activation/Cope rearrangement [J].

Davies, HML ;

Jin, QH .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5472-5475

[9] New strategic reactions for organic synthesis:: Catalytic asymmetric C-H activation α to nitrogen as a surrogate for the Mannich reaction [J].

Davies, HML ;

Venkataramani, C ;

Hansen, T ;

Hopper, DW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) :6462-6468

[10] New strategic reactions for organic synthesis:: Catalytic asymmetric C-H activation α to oxygen as a surrogate to the aldol reaction [J].

Davies, HML ;

Beckwith, REJ ;

Antoulinakis, EG ;

Jin, QH .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6126-6132

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