Phosphine-Mediated Olefination between Aldehydes and Allenes: An Efficient Synthesis of Trisubstituted 1,3-Dienes with High E-Selectivity

被引：58
作者：
Xu, Silong
Zhou, Lili
Zeng, San
Ma, Renqin
Wang, Zhihong
He, Zhengjie [1 ]
机构：
[1] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 15期
基金：
中国国家自然科学基金;
关键词：
CATALYZED 3+2 CYCLOADDITION; DIASTEREOSELECTIVE SYNTHESIS; 1,3,5-TRIAZA-7-PHOSPHAADAMANTANE PTA; ALLYLIC COMPOUNDS; ANNULATION; ALKYNES; CARBON; ALLENOATES; CHEMISTRY; MECHANISM;
D O I：
10.1021/ol901334c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The phosphine-mediated olefination of aldehydes with electron-deficient allenes to afford trisubstituted conjugated dienes in fair to excellent yields with high E-selectivity is described. The reaction represents a new reactivity pattern of allenes with aldehydes and also provides a highly stereoselective synthetic method for preparing conjugated dienes. In the reaction, the phosphine acts as a nucleophilic promoter to generate in situ an active phosphorus ylide which mediates the intermolecular olefination.
引用
收藏
页码：3498 / 3501
页数：4
相关论文
共 61 条
[1]   Novel DPPH radical scavengers, bisorbicillinol and demethyltrichodimerol, from a fungus [J].
Abe, N ;
Murata, T ;
Hirota, A .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1998, 62 (04) :661-666
[2]  
Ager D.J., 1990, ORGANIC REACTIONS, V38, P1, DOI [DOI 10.1002/0471264180.0R038.01, 10.1002/0471264180.or038.01]
[3]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[4]   The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds [J].
Blakemore, PR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2563-2585
[5]   Farinosones A-C, neurotrophic alkaloidal metabolites from the entomogenous deuteromycete Paecilomyces farinosus [J].
Cheng, YX ;
Schneider, B ;
Riese, U ;
Schubert, B ;
Li, ZZ ;
Hamburger, M .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (11) :1854-1858
[6]   Rhodium-catalyzed reaction of aryl and alkenylboronic acids with 2,4-dienoate esters:: Conjugate addition and Heck reaction products [J].
de la Herrán, G ;
Murcia, C ;
Csáky, AG .
ORGANIC LETTERS, 2005, 7 (25) :5629-5632
[7]   Functionalized 1-alkoxy-1,3-dienes: Their preparation and applications in synthetic organic [J].
Deagostino, Annamaria ;
Prandi, Cristina ;
Zavattaro, Chiara ;
Venturello, Paolo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (11) :2463-2483
[8]   Isolation and phytotoxicity of apocarotenoids from Chenopodium album [J].
DellaGreca, M ;
Di Marino, C ;
Zarrelli, A ;
D'Abrosca, B .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (09) :1492-1495
[9]  
Devon T.K., 1972, HDB NATURALLY OCCURR, VII.
[10]   Enyne metathesis (enyne bond reorganization) [J].
Diver, ST ;
Giessert, AJ .
CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382
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