Rhodium-catalyzed enantio- and diastereoselective intramolecular [2+2+2] cycloaddition of unsymmetrical dienynes

被引:30
作者
Sagae, Hiromi [1 ]
Noguchi, Keiichi [2 ]
Hirano, Masao [1 ]
Tanaka, Ken [1 ]
机构
[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Koganei, Tokyo 1848588, Japan
[2] Tokyo Univ Agr & Technol, Instrumentat Anal Ctr, Koganei, Tokyo 1848588, Japan
关键词
D O I
10.1039/b804294b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A cationic rhodium(I)/(R)-H-8-BINAP or (R)-Segphos complex catalyzes an intramolecular 12 + 2 + 21 cycloaddition of unsymmetrical dienynes, leading to fused tri- and tetracyclic cyclohexenes bearing two tertiary or quaternary carbon centers in high yields with high enantio- and diastereoselectivity.
引用
收藏
页码:3804 / 3806
页数:3
相关论文
共 24 条
[1]  
Agenet N., 2007, ORG REACT, V68, P1, DOI DOI 10.1002/0471264180.0R068.01
[2]   [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].
Chopade, Pramod R. ;
Louie, Janis .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327
[3]   Stereoselective formation of quaternary carbon centers and related functions [J].
Denissova, I ;
Barriault, L .
TETRAHEDRON, 2003, 59 (51) :10105-10146
[4]   Catalytic asymmetric synthesis of all-carbon quaternary stereocenters [J].
Douglas, CJ ;
Overman, LE .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5363-5367
[5]   Regio- and enantioselective intermolecular rhodium-catalyzed [2+2+2] carbocyclization reactions of 1,6-enynes with methyl arylpropiolates [J].
Evans, PA ;
Lai, KW ;
Sawyer, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) :12466-12467
[6]   Recent progress in cobalt-mediated [2+2+2] cycloaddition reactions [J].
Gandon, Vincent ;
Aubert, Corinne ;
Malacria, Max .
CHEMICAL COMMUNICATIONS, 2006, (21) :2209-2217
[7]   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
[8]   Transition metal catalyzed [2+2+2] cycloaddition and application in organic synthesis [J].
Kotha, S ;
Brahmachary, E ;
Lahiri, K .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (22) :4741-4767
[9]   ASYMMETRIC-SYNTHESIS OF ISOINDOLINE, AND ISOQUINOLINE DERIVATIVES USING NICKEL(0)-CATALYZED [2+2+2]-COCYCLIZATION [J].
SATO, Y ;
NISHIMATA, T ;
MORI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6133-6135
[10]   Novel chemoselectivity and stereochemical aspects of nickel-catalyzed [2+2+2] cycloadditions [J].
Seo, J ;
Chui, HMP ;
Heeg, MJ ;
Montgomery, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :476-477