Rhodium-catalyzed [2+2+2]cycloaddition of 1,6-diynes with isothiocyanates and carbon disulfide

被引：39

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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 05期

关键词：

D O I：

10.1021/ol053044r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A neutral rhodium(I)/BINAP complex effectively catalyzed a [2+2+2] cycloaddition of 1,6-diynes with isothiocyanates to give bicyclic thiopyranimines in 59-98% isolated yield. The reaction with carbon disulfide also proceeded to give bicyclic dithiopyrones in 74-85% isolated yield.

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页码：907 / 909

页数：3

相关论文

共 20 条

[1] The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane. [J].

Beesley, RM ;

Ingold, CK ;

Thorpe, JF .

JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 :1080-1106

[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] 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

[4] 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

[5] A RHODIUM-CATALYZED SYNTHESIS OF PYRIDONES [J].

FLYNN, ST ;

HASSOHENDERSON, SE ;

PARKINS, AW .

JOURNAL OF MOLECULAR CATALYSIS, 1985, 32 (01) :101-105

[6]

HOBERG H, 1982, SYNTHESIS-STUTTGART, P324

[7]

Hong P., 1977, TETRAHEDRON LETT, P1333

[8] GEM-DIALKYL EFFECT IN THE INTRAMOLECULAR DIELS-ALDER REACTION OF 2-FURFURYL METHYL FUMARATES - THE REACTIVE ROTAMER EFFECT, ENTHALPIC BASIS FOR ACCELERATION, AND EVIDENCE FOR A POLAR TRANSITION-STATE [J].

JUNG, ME ;

GERVAY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :224-232

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

Tanaka, K ;

Wada, A ;

Noguchi, K .

ORGANIC LETTERS, 2005, 7 (21) :4737-4739

[10] Enantioselective synthesis of axially chiral biaryls through rhodium-catalyzed complete intermolecular cross-cyclotrimerization of internal alkynes [J].

Tanaka, K ;

Nishida, G ;

Ogino, M ;

Hirano, M ;

Noguchi, K .

ORGANIC LETTERS, 2005, 7 (14) :3119-3121