Stereocontrolled synthesis of tetrasubstituted olefins

被引:549
作者
Flynn, Alison B. [1 ]
Ogilvie, William W. [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
关键词
D O I
10.1021/cr050051k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The four different carbon-linked groups' tetrasubstituted olefins are involved in materials research because useful, structural and electronic properties that may arise from the presence of the double bond. The stereoselective synthesis of tetrasubsitutted olefins has become a challenge in organic synthesis. There are many methods have been developed and the majority of the explored routes have used alkynyl carbometallation strategies. Other methods used are classical double bond-forming methods, the Wittig and Horner-Wadsworth-Emmons reaction was also used for the formation of tetrasubstituted double bonds, however, this method encounter serious problems of generality and stereoselectivity. The McMurry coupling that have been successful in producing highly congested products, however, sterochemistry can only be controlled in cyclic cases. Today, there are strategies such as olefin metathesis, radical sequences and ynolate chemistry are starting to emerge as viable techniques for the formation of tetrasubstituted olefins and offering potential in this area.
引用
收藏
页码:4698 / 4745
页数:48
相关论文
共 383 条
[1]   Ruthenium carbene complexes with imidazolin-2-ylidene ligands allow the formation of tetrasubstituted cycloalkenes by RCM [J].
Ackermann, L ;
Fürstner, A ;
Weskamp, T ;
Kohl, FJ ;
Herrmann, WA .
TETRAHEDRON LETTERS, 1999, 40 (26) :4787-4790
[2]   Steric and stereoelectronic control of the mode selectivity as a function of alkene structure in the reaction with dimethyl alpha-peroxy lactone: Cycloadducts and ene products versus epoxides [J].
Adam, W ;
Blancafort, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) :4778-4787
[3]   Intramolecular Ar-O-Ar bond formation in calixarenes [J].
Agbaria, K ;
Biali, SE .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5482-5489
[4]   TUNGSTEN WITTIG REAGENTS - AN EFFICIENT SYNTHESIS OF ALPHA-FUNCTIONALIZED TRI-SUBSTITUTED AND TETRA-SUBSTITUTED ALKENES [J].
AGUERO, A ;
KRESS, J ;
OSBORN, JA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (07) :531-533
[5]   STEREOSELECTIVE SYNTHESIS OF BETA-OXY-GAMMA-BUTYROLACTONES AND ALPHA-METHYLENE-GAMMA-BUTYROLACTONES ON PYRANOSE TEMPLATES [J].
ALABED, Y ;
ALTEL, TH ;
VOELTER, W .
TETRAHEDRON, 1993, 49 (41) :9295-9306
[6]   ALKENYL COPPER REAGENTS .18. CARBOCUPRATION OF ACETYLENIC ACETALS AND KETALS SYNTHESIS OF MANICONE, GERANIAL AND 2,4 (E,Z)-DIENALS [J].
ALEXAKIS, A ;
COMMERCON, A ;
COULENTIANOS, C ;
NORMANT, JF .
TETRAHEDRON, 1984, 40 (04) :715-731
[7]  
ALHASSAN MI, 1987, SYNTHESIS-STUTTGART, P816
[8]   3,5-bis(trifluoromethyl)phenyl sulfones in the Julia-Kocienski olefination - Application to the synthesis of tri- and tetrasubstituted olefins [J].
Alonso, Diego A. ;
Fuensanta, Monica ;
Najera, Carmen .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (20) :4747-4754
[9]   THE SYNTHESIS OF TRISUBSTITUTED CYCLOPENTADIENES AND THEIR REACTIVITY IN THE INTRAMOLECULAR DIELS-ALDER REACTION [J].
ALWARD, SJ ;
FALLIS, AG .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (01) :121-127
[10]   Total synthesis of paniculide A from D-glucose [J].
Amano, S ;
Takemura, N ;
Ohtsuka, M ;
Ogawa, S ;
Chida, N .
TETRAHEDRON, 1999, 55 (13) :3855-3870