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

被引：66

作者：

Davies, HML ^{[1
]}

Jin, QH ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 35期

关键词：

D O I：

10.1021/ja047185k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Rh2(S-DOSP)4-catalyzed reaction of vinyldiazoacetates with dihydronaphthalenes results in a highly enantioselective (91-99.6% ee) and diastereoselective (>98% de) C-H functionalization. The apparent intermolecular C-H insertion was demonstrated to be a combined C-H activation/Cope rearrangement followed by a retro-Cope rearrangement. Copyright © 2003 American Chemical Society.

引用

页码：10862 / 10863

页数：2

共 16 条

[1] Nucleophilic displacement at benzhydryl centers: Asymmetric synthesis of 1,1-diarylalkyl derivatives
Bolshan, Y
Chen, CY
Chilenski, JR
Gosselin, F
Mathre, DJ
O'Shea, PD
Roy, A
Tillyer, RD
[J]. ORGANIC LETTERS, 2004, 6 (01) : 111 - 114
[2] Cesati RR, 2004, J AM CHEM SOC, V126, P96
[3] Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion
Davies, HML
Beckwith, REJ
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2861 - 2903
[4] Catalytic asymmetric reactions for organic synthesis: The combined C-H activation/Cope rearrangement
Davies, HML
Jin, QH
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5472 - 5475
[5] New strategic reactions for organic synthesis:: Catalytic asymmetric C-H activation α to nitrogen as a surrogate for the Mannich reaction
Davies, HML
Venkataramani, C
Hansen, T
Hopper, DW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) : 6462 - 6468
[6] New strategic reactions for organic synthesis:: Catalytic asymmetric C-H activation α to oxygen as a surrogate to the aldol reaction
Davies, HML
Beckwith, REJ
Antoulinakis, EG
Jin, QH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) : 6126 - 6132
[7] Catalytic asymmetric benzylic C-H activation by means of carbenoid-induced C-H insertions
Davies, HML
Jin, QH
Ren, PD
Kovalevsky, AY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) : 4165 - 4169
[8] Catalytic asymmetric allylic C-H activation as a surrogate of the asymmetric Claisen rearrangement
Davies, HML
Ren, PD
Jin, QH
[J]. ORGANIC LETTERS, 2001, 3 (22) : 3587 - 3590
[9] Catalytic asymmetric C-H activation of silyl enol ethers as an equivalent of an asymmetric Michael reaction
Davies, HML
Ren, PD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) : 2070 - 2071
[10] Kinetic resolution and double stereodifferentiation in catalytic asymmetric C-H activation of 2-substituted pyrrolidines
Davies, HML
Venkataramani, C
[J]. ORGANIC LETTERS, 2001, 3 (11) : 1773 - 1775

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