Enantioselective Carbene Cascade: An Effective Approach to Cyclopentadienes and Applications in Diels-Alder Reactions

被引：40

作者：

Wang, Xiangbo ^{[1
]}

Zhou, Yunfei ^{[1
]}

Qiu, Lihua ^{[1
]}

Yao, Ruwei ^{[1
]}

Zheng, Yang ^{[1
]}

Zhang, Cheng ^{[1
]}

Bao, Xiaoguang ^{[1
]}

Xu, Xinfang ^{[1
]}

机构：

[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 10期

关键词：

cascade reactions; cycloaddition; cyclopentadienes; diazo compounds; dirhodium catalysts; metal carbenes; H BOND INSERTION; 3+2 CYCLOADDITION; CATALYZED CYCLOISOMERIZATION; CYCLOPROPENES; DERIVATIVES; REARRANGEMENT; CYCLIZATION; INHIBITORS; ALKYNES;

D O I：

10.1002/adsc.201501106

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An asymmetric carbene cascade reaction, which proceeds through carbene/alkyne metathesis and formal (3 + 2) cycloaddition and converts alkynyl-tethered enol diazoacetates to chiral bicyclic cyclopentadienes, is presented; and no catalytic asymmetric version of these carbene cascade transformations has been disclosed so far. The proton signals of the cyclopropene intermediates are observed in the mechanism study, which clearly demonstrate the reaction pathways. In addition, these products are intercepted via Diels-Alder reactions to provide bridged polycyclic structures in high yields and enantioselectivities.

引用

页码：1571 / 1576

页数：6

共 50 条

[31] SYNTHESIS OF SUBSTITUTED CYCLOPENTADIENES - INTRAMOLECULAR DIELS-ALDER PRECURSORS
STERNBACH, DD
HUGHES, JW
BURDI, DF
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (01): : 201 - 202
[32] DIELS-ALDER REACTIONS OF CYCLOALKENONES .21. DIELS-ALDER REACTIONS OF (+)-APOVERBENONE
MINUTI, L
SELVAGGI, R
TATICCHI, A
GACSBAITZ, E
MATCHYTKA, D
SYNTHETIC COMMUNICATIONS, 1991, 21 (21) : 2143 - 2155
[33] Enantioselective synthesis of (+)-chamaecypanone C and analogs using a tandem retro-Diels-Alder/Diels-Alder cascade
Dong, Suwei
Hamel, Ernest
Beutler, John A.
Porco, John A., Jr.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[34] PHOTOCHEMICAL INTRAMOLECULAR DIELS-ALDER REACTIONS OF 1-SUBSTITUTED CYCLOPENTADIENES BY TRIPLEX FORMATION
YOON, HJ
CHUNG, WS
JANG, BB
CHAE, WK
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1995, 16 (09) : 792 - 793
[35] Carbon-substituted Co(III) salens as effective catalysts for enantioselective Diels-Alder reactions
McGilvra, JD
Rawai, VH
SYNLETT, 2004, (13) : 2440 - 2442
[36] Substituent effects in the Diels-Alder reactions of butadienes, cyclopentadienes, furans and pyroles with maleic anhydride
Qiu, Yongge
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2015, 28 (05) : 370 - 376
[37] SYNTHESIS AND DIELS-ALDER REACTIONS OF 1-ACYLATED 1,3-CYCLOPENTADIENES
GRUNDKE, G
HOFFMANN, HMR
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (26): : 5428 - 5431
[38] Chiral N-heterocyclic carbene catalyzed, enantioselective oxodiene Diels-Alder reactions with low catalyst loadings
He, Ming
Uc, Gerson J.
Bode, Jeffrey W.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) : 15088 - 15089
[39] Chiral N-heterocyclic carbene catalyzed, enantioselective oxodiene diels-alder reactions with low catalyst loadings
He, Ming
Uc, Gerson J.
Bode, Jeffrey W.
Journal of the American Chemical Society, 2006, 128 (47): : 15088 - 15089
[40] ASYMMETRIC DIELS-ALDER REACTIONS OF N-ACYLAMINO CARBENE COMPLEXES
WULFF, WD
POWERS, TS
ANDERSON, BA
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 107 - ORGN

← 1 2 3 4 5 →