Highly enantioselective spiro cyclization of 1,6-enynes catalyzed by cationic skewphos rhodium(I) complex

被引:39
作者
Mikami, K [1 ]
Yusa, Y [1 ]
Hatano, M [1 ]
Wakabayashi, K [1 ]
Aikawa, K [1 ]
机构
[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan
关键词
D O I
10.1039/b310789b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A cationic rhodium(I) complex having a skewphos ligand is shown to be a highly enantioselective catalyst for asymmetric carbocyclization of 1,6-enynes with tri-substituted olefins to control quaternary stereogenic centers of spiro-rings.
引用
收藏
页码:98 / 99
页数:2
相关论文
共 35 条
[1]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[2]   CATALYTIC AND STRUCTURAL STUDIES OF RHI COMPLEXES OF (-)-(2S,4S)-2,4-BIS(DIPHENYLPHOSPHINO)PENTANE - ASYMMETRIC HYDROGENATION OF ACETOPHENONEBENZYLIMINE AND ACETOPHENONE [J].
BAKOS, J ;
TOTH, I ;
HEIL, B ;
SZALONTAI, G ;
PARKANYI, L ;
FULOP, V .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 370 (1-3) :263-276
[3]   A FACILE METHOD FOR THE PREPARATION OF 2,4-BIS(DIPHENYLPHOSPHINO)PENTANE (BDPP) ENANTIOMERS AND THEIR APPLICATION IN ASYMMETRIC HYDROGENATION [J].
BAKOS, J ;
TOTH, I ;
HEIL, B ;
MARKO, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 279 (1-2) :23-29
[4]   In situ and reactor study of the enantioselective hydrogenation of acetylacetone by ruthenium catalysis with the new chiral diphosphine ligand (R)-(R)-3-benzyl-2,4-bis(diphenylphosphino)pentane [J].
Bianchini, C ;
Barbaro, P ;
Scapacci, G ;
Zanobini, F .
ORGANOMETALLICS, 2000, 19 (13) :2450-2461
[5]  
Cao P, 2000, ANGEW CHEM INT EDIT, V39, P4104, DOI 10.1002/1521-3773(20001117)39:22<4104::AID-ANIE4104>3.0.CO
[6]  
2-X
[7]   Enantioselective cycloisomerization of 1,6-enynes catalyzed by chiral diphosphane-palladium complexes [J].
Goeke, A ;
Sawamura, M ;
Kuwano, R ;
Ito, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (06) :662-663
[8]   NOVEL COORDINATION CHEMISTRY AND CATALYTIC PROPERTIES OF CATIONIC 1,2-BIS(DIPHENYLPHOSPHINO)ETHANERHODIUM(I) COMPLEXES [J].
HALPERN, J ;
RILEY, DP ;
CHAN, ASC ;
PLUTH, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (24) :8055-8057
[9]   Highly enantioselective quinoline synthesis via ene-type cyclization of 1,7-enynes catalyzed by a cationic BINAP-palladium(II) complex [J].
Hatano, M ;
Mikami, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (16) :4704-4705
[10]   Highly enantioselective ene-type spiro-cyclization of allyl propargyl ethers catalyzed by cationic palladium(II) complexes with a new type of PN-ligand bearing achiral gem-dimethyl oxazoline [J].
Hatano, M ;
Mikami, K .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 196 (1-2) :165-169