Intermolecular rhodium-catalyzed [2+2+2] carbocyclization reactions of 1,6-enynes with symmetrical and unsymmetrical alkynes

被引:34
作者
Evans, PA [1 ]
Sawyer, JR [1 ]
Lai, KW [1 ]
Huffman, JC [1 ]
机构
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
关键词
D O I
10.1039/b505383h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The crossed intermolecular rhodium-catalyzed [2 + 2 + 2] carbocyclization of carbon and heteroatom tethered 1,6-enynes can be accomplished with symmetrical and unsymmetrical alkynes, to afford the corresponding bicyclohexadienes in an efficient and highly selective manner.
引用
收藏
页码:3971 / 3973
页数:3
相关论文
共 20 条
[1]   INTERMOLECULAR COBALT-MEDIATED [2+2+2]CYCLOADDITIONS - REGIOSPECIFIC ONE-STEP CONSTRUCTION OF BICYCLIC DIENES FROM ALPHA,OMEGA-ENYNES AND ALKYNES [J].
CHANG, CA ;
KING, JA ;
VOLLHARDT, KPC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (02) :53-55
[2]   The dimerization and cyclotrimerization of acetylenes mediated by phosphine complexes of cobalt(I), rhodium(I), and iridium(I) [J].
Field, LD ;
Ward, AJ ;
Turner, P .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (11) :1085-1092
[3]  
Fujiwara M, 2005, MODERN RHODIUM-CATALYZED ORGANIC REACTIONS, P129, DOI 10.1002/3527604693.ch7
[4]   RHODIUM-CATALYZED [2+2+2]-CYCLOADDITIONS OF ACETYLENES [J].
GRIGG, R ;
SCOTT, R ;
STEVENSON, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1357-1364
[5]   RHODIUM(I)-CATALYZED REACTIONS OF ENYNES - LINEAR COUPLING VS CYCLO-ADDITION [J].
GRIGG, R ;
SCOTT, R ;
STEVENSON, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1365-1369
[6]   Iridium complex-catalyzed reaction of 1,6-enynes: Cycloaddition and cycloisomerization [J].
Kezuka, S ;
Okado, T ;
Niou, E ;
Takeuchi, R .
ORGANIC LETTERS, 2005, 7 (09) :1711-1714
[7]   Rhodium-catalyzed [2+2+2] cyclotrimerization in an aqueous-organic biphasic system [J].
Kinoshita, H ;
Shinokubo, H ;
Ohsima, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7784-7785
[8]  
Malacria M., 2001, SCI SYNTHESIS HOUBEN, V1, P439
[9]   RHODIUM-CATALYZED ALKYNE CYCLOTRIMERIZATION STRATEGIES FOR C-ARYLGLYCOSIDE SYNTHESIS [J].
MCDONALD, FE ;
ZHU, HYH ;
HOLMQUIST, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (24) :6605-6606
[10]   Novel metallacycle complexes from bis(oxazolinyl)pyridine-rhodium(I) species and diynes [J].
Nishiyama, H ;
Niwa, E ;
Inoue, T ;
Ishima, Y ;
Aoki, K .
ORGANOMETALLICS, 2002, 21 (13) :2572-2574