Organocatalytic C-C bond activation of cyclopropenones for ring-opening formal [3+2] cycloaddition with isatins

被引：39

作者：

Xu, Junyu ^{[1
]}

Cao, Jing ^{[1
]}

Fang, Chao ^{[1
]}

Lu, Tao ^{[1
]}

Du, Ding ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Organ Chem, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 04期

基金：

中国国家自然科学基金;

关键词：

CARBON-CARBON BOND; CARBENE-CATALYZED REACTIONS; CPCO-MEDIATED REACTIONS; DIELS-ALDER ADDUCT; ALKYNYL ALDEHYDES; ACCESS; ANNULATION; 1,3-DIPHENYLISOBENZOFURAN; DIPHENYLCYCLOPROPENONE; SPIROOXINDOLES;

D O I：

10.1039/c6qo00734a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclopropenones were first applied as potential 3C synthons in ring-opening formal cycloaddition via an organocatalytic C-C bond activation strategy. This [3 + 2] cycloaddition of cyclopropenones with isatins catalyzed by using two different Lewis bases offers rapid access to spirooxindoles 3 and 4 regioselectively. These findings will provide helpful guidelines for further investigation of the reactivity of cyclopropenones with organocatalysis.

引用

页码：560 / 564

页数：5

共 50 条

[31] OCTANE FROM THIOPHENE - RING-OPENING AND C-C COUPLING OF THIOPHENE BY RHODIUM COMPLEXES
JONES, WD
CHIN, RM
MYERS, A
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 351 - INOR
[32] Tungsten(II)-initiated ring-opening metathesis polymerization and other C-C bond forming reactions of 5-vinyl-2-norbornene
Gorski, Marcin
Szymanska-Buzar, Teresa
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 257 (1-2) : 41 - 47
[33] RING EXPANSION WITH 4 C-ATOMS BY TANDEM (2+2)CYCLOADDITION AND ELECTROCYCLIC RING-OPENING
VOS, GJM
REINHOUDT, DN
BENDERS, PH
HARKEMA, S
VANHUMMEL, GJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (10) : 661 - 662
[34] C-C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring-Opening Cyanation and Ethynylation of Cyclobutanol Derivatives
Ren, Rongguo
Wu, Zhen
Xu, Yan
Zhu, Chen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (08) : 2866 - 2869
[35] Synthesis of the AC ring of paclitaxel: Formation of the C ring by [3+2] cycloaddition with a preformed A ring
Nakai, K
Doi, T
Takahashi, T
SYNLETT, 2005, (05) : 866 - 868
[36] Catalytic asymmetric [3+2] cycloadditions about oxiranes by C-C bond cleavage of epoxides
Lin, Lili
Chen, Weiliang
Feng, Xiaoming
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
[37] Ring-Opening Ortho-C-H Allylation of Benzoic Acids with Vinylcyclopropanes: Merging Catalytic C-H and C-C Activation Concepts
Hu, Zhiyong
Hu, Xiao-Qiang
Zhang, Guodong
Goossben, Lukas J.
ORGANIC LETTERS, 2019, 21 (17) : 6770 - 6773
[38] An asymmetric [3+2] cycloaddition of alkynes with oxiranes by selective C-C bond cleavage of epoxides: highly efficient synthesis of chiral furan derivatives
Chen, Weiliang
Fu, Xuan
Lin, Lili
Yuan, Xiao
Luo, Weiwei
Feng, Juhua
Liu, Xiaohua
Feng, Xiaoming
CHEMICAL COMMUNICATIONS, 2014, 50 (78) : 11480 - 11483
[39] C-C BOND ACTIVATION OF CYCLOPROPANE RING IN HYDROSILYLATION CATALYZED BY WILKINSON COMPLEX
BESSMERTNYKH, AG
BLINOV, KA
GRISHIN, YK
DONSKAYA, NA
BELETSKAYA, IP
TETRAHEDRON LETTERS, 1995, 36 (43) : 7901 - 7904
[40] Rapid domino [3+2] cycloaddition, [4+2] cycloreversion, ring-opening and aromatisation of a fused oxanorbornane substrate
Johnstone, Mark D.
Pfeffer, Frederick M.
TETRAHEDRON LETTERS, 2015, 56 (21) : 2754 - 2757

← 1 2 3 4 5 →