Nickel-Catalyzed Intermolecular [2+2] Cycloaddition of Conjugated Enynes with Alkenes

被引:113
作者
Nishimura, Akira [1 ]
Ohashi, Masato [1 ]
Ogoshi, Sensuke [1 ]
机构
[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
关键词
SILYL ENOL ETHERS; DIMETHYL ACETYLENEDICARBOXYLATE; CYCLOISOMERIZATION REACTIONS; NORBORNENE DERIVATIVES; REDUCTIVE ELIMINATION; ETHYL PROPIOLATE; COBALT COMPLEXES; ALKYNES; ESTERS; CYCLOBUTENES;
D O I
10.1021/ja3074775
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A nickel-catalyzed intermolecular [2 + 2] cycloaddition of conjugated enynes with alkenes has been developed. A variety of electron-deficient alkenes as well as electronically neutral norbornene and 1-decene were applicable to this reaction. The use of conjugated enynes circumvented possible side rections, such as oligomerizations and cyclotrimerizations. The isolation of reaction intermediate complexes revealed that the eta(3)-butadienyl coordination is the key for the selective formation of cyclobutene.
引用
收藏
页码:15692 / 15695
页数:4
相关论文
共 57 条
[1]   PtBr2-catalyzed consecutive enyne metathesis-aromatization of 1-(1-methoxy-but-3-enyl)-2-(1-alkynyl)benzenes:: Dual role of the Pt catalyst [J].
Bajracharya, GB ;
Nakamura, I ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :892-897
[2]   REACTIONS OF COORDINATED LIGANDS .57. SYNTHESIS, STRUCTURE AND INTERRELATIONSHIP OF 2-SIGMA-BUTADIENYL AND CATIONIC (1,2,3-ETA)-TRANS-BUTADIENYL-PLATINUM AND (1,2,3-ETA)-TRANS-BUTADIENYL-PALLADIUM COMPLEXES - CRYSTAL-STRUCTURES OF CIS-[PTCL(SIGMA-C(CH2)C(ET)=CH2)(DPPF)] AND [PT((1,2,3-ETA)-TRANS-CH2C(ET)C=CH2)(PPH3)2][PF6] [DPPF = 1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE] [J].
BENYUNES, SA ;
BRANDT, L ;
FRIES, A ;
GREEN, M ;
MAHON, MF ;
PAPWORTH, TMT .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (24) :3785-3793
[3]   SYNTHESIS AND REACTIVITY OF CATIONIC (ETA-3-BUTADIENYL)PLATINUM COMPLEXES [J].
BENYUNES, SA ;
BRANDT, L ;
GREEN, M ;
PARKINS, AW .
ORGANOMETALLICS, 1991, 10 (01) :57-59
[4]   Cross [2+2] cycloaddition of bicyclic alkenes with alkynes mediated by cobalt complexes: A facile synthesis of cyclobutene derivatives [J].
Chao, KC ;
Rayabarapu, DK ;
Wang, CC ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :8804-8810
[5]   [2+2] CYCLOADDITIONS OF SILYL ENOL ETHERS AND DIMETHYL ACETYLENEDICARBOXYLATE, DIMETHYL FUMARATE, AND METHYL CROTONATE [J].
CLARK, RD ;
UNTCH, KG .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (02) :253-255
[6]   [2+2] CYCLOADDITION OF ETHYL PROPIOLATE AND SILYL ENOL ETHERS [J].
CLARK, RD ;
UNTCH, KG .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (02) :248-253
[7]   Studies related to the total synthesis of the sesquiterpene core of the pyrrolobenzoxazine natural products CJ-12662 and CJ-12663 [J].
Commandeur, Malgorzata ;
Commandeur, Claude ;
De Paolis, Michael ;
Edmunds, Andrew J. F. ;
Maienfisch, Peter ;
Ghosez, Leon .
TETRAHEDRON LETTERS, 2009, 50 (26) :3359-3362
[8]   Bioactive cyclobutane-containing alkaloids [J].
Dembitsky, Valery M. .
JOURNAL OF NATURAL MEDICINES, 2008, 62 (01) :1-33
[9]   SYNTHESIS OF NEW TYPES OF TETRACYCLO[4.3.0.02,4.03,7]NONANE HYDROCARBONS BY CYCLOCODIMERIZATION OF NORBORNADIENE AND ITS DERIVATIVES WITH DIACETYLENES AND VINYLACETYLENES, CATALYZED BY LOW-VALENCE COBALT COMPLEXES [J].
DZHEMILEV, UM ;
KHUSNUTDINOV, RI ;
MUSLIMOV, ZS ;
TOLSTIKOV, GA .
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1987, 36 (05) :977-982
[10]   Ligand-Controlled Enantioselective [2+2] Cycloaddition of Oxabicyclic Alkenes with Terminal Alkynes Using Chiral Iridium Catalysts [J].
Fan, Bao-Min ;
Li, Xiao-Jiao ;
Peng, Fang-Zhi ;
Zhang, Hong-Bin ;
Chan, Albert S. C. ;
Shao, Zhi-Hui .
ORGANIC LETTERS, 2010, 12 (02) :304-306