Alkenes in [2+2+2] Cycloadditions

被引:112
作者
Dominguez, Gema [1 ]
Perez-Castells, Javier [1 ]
机构
[1] Univ San Pablo CEU, Dept Chem & Biochem, E-28668 Madrid, Spain
关键词
alkenes; cyclotrimerization; heterocycles; homogeneous catalysis; transition metals; PALLADIUM-CATALYZED CYCLOCOTRIMERIZATION; GASEOUS ALKYNE EQUIVALENTS; LIQUID ENOL ETHERS; N-H ACTIVATION; ENANTIOSELECTIVE CONSTRUCTION; CHEMOSELECTIVE COCYCLOTRIMERIZATION; REGIOSELECTIVE CYCLOTRIMERIZATION; CARBOCYCLIZATION REACTIONS; STEREOSELECTIVE-SYNTHESIS; COBALT METALLOCYCLES;
D O I
10.1002/chem.201504987
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Participation of alkenes and allenes in [2+2+2] cycloaddition reactions has attracted much attention recently. This version of the well-established alkyne cyclotrimerization renders interesting products, such as cyclohexadienes and other polycycles, through cascade processes. Many mechanistic variations are observed when using certain metal complexes as catalysts. The frequent generation of stereogenic centers has prompted the development of efficient asymmetric versions. This Minireview summarizes the efforts reported to date on the use of double bonds as partners in [2+2+2] cyclotrimerizations.
引用
收藏
页码:6720 / 6739
页数:20
相关论文
共 173 条
[61]   NI(0) CATALYZED PREPARATION OF DELTA-LACTAMS FROM ISOPRENE AND PHENYLISOCYANATE [J].
HOBERG, H ;
BARHAUSEN, D .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 397 (01) :C20-C23
[62]   NOVEL NI(0) CATALYZED INTERACTION OF 1,3-BUTADIENE AND PHENYLISOCYANATE [J].
HOBERG, H ;
BARHAUSEN, D ;
MYNOTT, R ;
SCHROTH, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 410 (01) :117-126
[63]   Nickel-promoted first ene-diyne cycloaddition reaction on C60:: Synthesis and photochemistry of the fullerene derivatives [J].
Hsiao, TY ;
Santhosh, KC ;
Liou, KF ;
Cheng, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (47) :12232-12236
[64]   Nickel-catalyzed highly chemoselective cocyclotrimerization of arynes with allenes: a novel method for 10-methylene-9,10-dihydrophenanthrenes [J].
Hsieh, JC ;
Rayabarapu, DK ;
Cheng, CH .
CHEMICAL COMMUNICATIONS, 2004, (05) :532-533
[65]   Nickel-catalyzed cocyclotrimerization of oxa- and azabenzonorbornadienes with alkynes: reaction with multiple synthetic applications [J].
Huang, DJ ;
Sambaiah, T ;
Cheng, CH .
NEW JOURNAL OF CHEMISTRY, 1998, 22 (11) :1147-1149
[66]   Gold-catalyzed diastereoselective [2+2+2]-cycloaddition of 1,7-enynes with carbonyl compounds [J].
Huple, Deepak B. ;
Liu, Rai-Shung .
CHEMICAL COMMUNICATIONS, 2012, 48 (89) :10975-10977
[67]   Catalytic enantioselective intermolecular [2+2+2] cycloaddition of an alkene and two alkynes [J].
Ikeda, S ;
Kondo, H ;
Arii, T ;
Odashima, K .
CHEMICAL COMMUNICATIONS, 2002, (20) :2422-2423
[68]   Nickel- and zinc-promoted [2+2+2] cycloaddition of diynes and α,β-enones [J].
Ikeda, S ;
Watanabe, H ;
Sato, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :7026-7029
[69]   Regioselective cyclic cotrimerization of alpha,beta-enones and alkynes by a nickel-aluminum catalyst system [J].
Ikeda, S ;
Mori, N ;
Sato, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (20) :4779-4780
[70]   Effects of monodentate oxazoline ligands in Ni/Al-catalyzed regioselective cyclotrimerization of enones and alkynes [J].
Ikeda, S ;
Kondo, H ;
Mori, N .
CHEMICAL COMMUNICATIONS, 2000, (10) :815-816