Highly Stereoselective Synthesis of Trisubstituted cis-[3]Cumulenols from Alkynylated Oxatitanacycles in the Presence of Lewis acids

被引:13
作者
Chen, Jingjin [1 ]
Liu, Yuanhong [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
FACILE SYNTHESIS; CYCLOPENTADIENE DERIVATIVES; TETRAHYDROFURAN DERIVATIVES; CATALYZED DIMERIZATION; MEDIATED REACTIONS; AROYL CYANIDES; ALKYNES; ALDEHYDES; ZIRCONIUM; CUMULENE;
D O I
10.1021/om900941y
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A highly efficient and stereoselective method for the synthesis of trisubstituted cis-[3]cumulenols via oxatitana-cycles derived from titanium-mediated coupling of 1,3-butadiynes with aldehydes or ketones promoted by Lewis-acids is described.
引用
收藏
页码:505 / 508
页数:4
相关论文
共 45 条
[1]   Synthesis of trisubstituted furans from epoxypropargyl esters by sequential SmI2-promoted reduction-elimination and Pd(II)-catalyzed cycloisomerization [J].
Aurrecoechea, JM ;
Pérez, E ;
Solay, M .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :564-569
[3]  
Brandsma L., 1981, SYNTHESIS ACETYLENES
[4]  
CAO XP, 1995, J CHEM SOC P1, P193
[5]   Dialkyltitanium-mediated titanation of conjugated 1,3-butadiynes and its coupling reactions with aldehydes: a facile synthesis of stereodefined enynes and trans-enynols [J].
Chen, Jingjin ;
Liu, Yuanhong .
TETRAHEDRON LETTERS, 2008, 49 (47) :6655-6658
[6]   FACILE SYNTHESIS OF ALKYL AND ARYL SUBSTITUTED 1,2,3-BUTATRIENES [J].
CHOW, HF ;
CAO, XP ;
LEUNG, MK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2121-2122
[7]   Site-selective mono-titanation of conjugated diynes with a Ti(II) alkoxide reagent. Concise preparation of stereo-defined enynes and dienynes [J].
Delas, C ;
Urabe, H ;
Sato, F .
CHEMICAL COMMUNICATIONS, 2002, (03) :272-273
[8]   SYNTHETIC APPROACHES TOWARD MOLECULAR AND POLYMERIC CARBON ALLOTROPES [J].
DIEDERICH, F ;
RUBIN, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (09) :1101-1123
[9]  
Dzhemilev UM, 1997, MENDELEEV COMMUN, P198
[10]   Diverse Reactivity of Zirconacyclocumulenes Derived from Coupling of Benzynezirconocenes with 1,3-Butadiynes towards Acyl Cyanides: Synthesis of Indeno[2,1-b]pyrroles or [3]Cumulenones [J].
Fu, Xiaoping ;
Chen, Jingjin ;
Li, Guangyu ;
Liu, Yuanhong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (30) :5500-5504