Rhodium-catalyzed chemo-, regio-, and enantioselective [2+2+2] cycloaddition of alkynes with isocyanates

被引:121
作者
Tanaka, K [1 ]
Wada, A
Noguchi, K
机构
[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan
[2] Tokyo Univ Agr & Technol, Instrumentat Anal Ctr, Koganei, Tokyo 1848588, Japan
关键词
D O I
10.1021/ol052041b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have developed a cationic rhodium([)/modified-BINAP complex-catalyzed chemoselective [2 + 2 + 2] cycloaddition of alkynes with isocyanates leading to a wide range of 2-pyridones. This method was successfully applied to the chemo-, regio-, and enantioselective synthesis of axially chiral 2-pyridones from unsymmetrical alpha,omega,-diynes, bearing an ortho-substituted phenyl at one terminal position, and alkyl isocyanates.
引用
收藏
页码:4737 / 4739
页数:3
相关论文
共 43 条
[1]   HOMOGENEOUS AND BIPHASIC OLIGOMERIZATION OF TERMINAL ALKYNES BY SOME WATER-SOLUBLE RHODIUM CATALYSTS [J].
BAIDOSSI, W ;
GOREN, N ;
BLUM, J ;
SCHUMANN, H ;
HEMLING, H .
JOURNAL OF MOLECULAR CATALYSIS, 1993, 85 (02) :153-162
[2]   Synthesis of macrocycles via cobalt-mediated [2+2+2] cycloadditions [J].
Boñaga, LVR ;
Zhang, HC ;
Moretto, AF ;
Ye, H ;
Gauthier, DA ;
Li, J ;
Leo, GC ;
Maryanoff, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3473-3485
[3]   Cobalt-mediated macrocyclizations.: Facile synthesis of 2-oxo pyridinophanes via [2+2+2] cycloaddition of α,ω-diynes and isocyanates [J].
Boñaga, LVR ;
Zhang, HC ;
Gauthier, DA ;
Reddy, I ;
Maryanoff, BE .
ORGANIC LETTERS, 2003, 5 (24) :4537-4540
[4]   COBALT-CATALYZED CYCLO-COTRIMERIZATION OF ALKYNES AND HETEROCUMULENES [J].
DIVERSI, P ;
INGROSSO, G ;
LUCHERINI, A ;
MALQUORI, S .
JOURNAL OF MOLECULAR CATALYSIS, 1987, 40 (03) :267-280
[5]   HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE SILYLFORMYLATION OF ALKYNES UNDER MILD CONDITIONS PROMOTED BY DIRHODIUM(II) PERFLUOROBUTYRATE [J].
DOYLE, MP ;
SHANKLIN, MS .
ORGANOMETALLICS, 1994, 13 (04) :1081-1088
[6]   Nickel-catalyzed cycloaddition of alkynes and isocyanates [J].
Duong, HA ;
Cross, MJ ;
Louie, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (37) :11438-11439
[7]   THE PREPARATION OF 2(1H)-PYRIDINONES AND 2,3-DIHYDRO-5(1H)-INDOLIZINONES VIA TRANSITION-METAL MEDIATED COCYCLIZATION OF ALKYNES AND ISOCYANATES - A NOVEL CONSTRUCTION OF THE ANTITUMOR AGENT CAMPTOTHECIN [J].
EARL, RA ;
VOLLHARDT, KPC .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (25) :4786-4800
[8]   A RHODIUM-CATALYZED SYNTHESIS OF PYRIDONES [J].
FLYNN, ST ;
HASSOHENDERSON, SE ;
PARKINS, AW .
JOURNAL OF MOLECULAR CATALYSIS, 1985, 32 (01) :101-105
[9]   N-prop-2-ynylmaleimide.: Application to sequential one-pot Rh(I) catalysed [2+2+2]-alkyne cyclotrimerisation-imine cycloaddition [J].
Grigg, R ;
Sridharan, V ;
Wang, J ;
Xu, J .
TETRAHEDRON, 2000, 56 (45) :8967-8976
[10]   RHODIUM CATALYZED [2+2+2] CYCLO-ADDITIONS OF ACETYLENES [J].
GRIGG, R ;
SCOTT, R ;
STEVENSON, P .
TETRAHEDRON LETTERS, 1982, 23 (26) :2691-2692