An improved 1,3-diene synthesis from alkyne and ethylene using cross-enyne metathesis

被引：81

作者：

Tonogaki, K ^{[1
]}

Mori, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(02)00215-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of 1,3-diene from alkyne and ethylene (I atm) was improved using ruthenium carbene complex lb having heterocyclic carbene as a ligand. In this reaction, the heteroatom at the propargylic position was not required, although the reaction of alkyne with the first-generation ruthenium carbene complex la was affected by the substituent at the propargylic position. Various 1,3-dienes could be synthesized from alkynes and ethylene. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：2235 / 2238

页数：4

共 50 条

[11] STEREO-DIRECTED SYNTHESIS OF FUNCTIONAL DERIVATIVES OF 1,3-DIENE AND 1,3-ENYNE HYDROCARBONS AND SILICON-HYDROCARBONS [J].

NESTEROV, NI ;

KOMISSAROVA, EV ;

BELYAEV, NN ;

STADNICHUK, MD ;

PETROV, AA .

ZHURNAL OBSHCHEI KHIMII, 1977, 47 (06) :1425-1426

[12] DIPOLE-MOMENTS AND STRUCTURE OF 1,3-ENYNE AND 1,3-DIENE ORGANIC AND ORGANOSILICON SULFONES [J].

MINGALEVA, KS ;

TANASKOV, MM ;

STADNICHUK, MD ;

PETROV, AA .

ZHURNAL OBSHCHEI KHIMII, 1977, 47 (10) :2278-2284

[13] A PRACTICAL SYNTHESIS OF 1,3-DIENE USING ALLYLTRIPHENYLSILANE AND TITANIUM TETRAISOPROPOXIDE [J].

IKEDA, Y ;

YAMAMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (02) :657-658

[14] Post-assembly peptide modification via cross-enyne metathesis, Diels-Alder reaction and 1,3-dipolar cycloaddition [J].

Goyal, Deepti ;

Kotha, Sambasivarao .

ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242

[15] Synthesis of unsymmetrical 1,3-diynes via alkyne cross-metathesis [J].

Li, Sin Ting ;

Schnabel, Tobias ;

Lysenko, Sergej ;

Brandhorst, Kai ;

Tamm, Matthias .

CHEMICAL COMMUNICATIONS, 2013, 49 (65) :7189-7191

[16] Synthesis of a Novel Taxa-Oxa-Sugar Hybrid Core Structure by Tandem Cross-Enyne Metathesis/IMDA [J].

Nandurdikar, Rahul S. ;

Subrahmanyam, Ayyagari V. ;

Kaliappan, Krishna P. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (14) :2788-2799

[17] Substituent-Enhanced Intermolecular Catalytic Ene-yne Metathesis for Efficient 1,3-Diene Synthesis [J].

Basemann, Kevin ;

Schmidt, Bradley M. ;

Sadow, Aaron D. .

ACS CATALYSIS, 2022, 12 (01) :226-234

[18] Design, synthesis, and applications of stereospecific 1,3-diene carbonyls [J].

Feng, Qiang ;

Wang, Shihui ;

Ma, Xingxing ;

Rao, Changqing ;

Song, Qiuling .

SCIENCE CHINA-CHEMISTRY, 2022, 65 (05) :912-917

[19] PHOTOCHEMICAL SYNTHESIS OF BIS(1,3-DIENE)MONOCARBONYLIRON COMPOUNDS [J].

KOERNERV.E ;

BUCHKREM.J ;

PFAIFER, Z ;

GREVELS, FW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (04) :260-&

[20] A GENERAL METHOD OF OBTAINING 1,3-DIENE COMPOUNDS FROM CORRESPONDING SATURATED AND ETHYLENE HYDROCARBONS [J].

TISHCHENKO, DV .

ZHURNAL OBSHCHEI KHIMII, 1947, 17 (03) :460-470

← 1 2 3 4 5 →