Epoxy ketones as versatile building blocks in organic synthesis

被引:119
作者
Lauret, C [1 ]
机构
[1] Univ Liverpool, Dept Chem, Robert Robinson Labs, Liverpool L7 7DB, Merseyside, England
关键词
D O I
10.1016/S0957-4166(01)00412-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The major advances made in the functionalisation of racemic and optically active epoxy ketones where one or several stereogenic centres are either preserved or modified are reviewed. Some relevant applications to the synthesis of natural products and biologically active compounds are also described. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2359 / 2383
页数:25
相关论文
共 146 条
[51]   Poly-L-leucine catalysed epoxidation reactions:: A short, stereoselective route to chiral α,β-epoxyalcohols [J].
Gillmore, AT ;
Roberts, SM ;
Hursthouse, MB ;
Malik, KMA .
TETRAHEDRON LETTERS, 1998, 39 (20) :3315-3318
[52]  
GLOTTER E, 1982, J CHEM RES-S, P32
[53]   FLAVANOID EPOXIDES .8. ACID AND BASE-CATALYZED REACTIONS OF 2'-TOSYLOXYCHALCONE EPOXIDES - MECHANISM OF ALGAR-FLYNN-OYAMADA REACTION [J].
GORMLEY, TR ;
OSULLIVA.WI .
TETRAHEDRON, 1973, 29 (02) :369-373
[54]   Asymmetric synthesis of the Abbott amino dihydroxyethylene dipeptide isostere subunit [J].
Haddad, M ;
Larcheveque, M .
TETRAHEDRON LETTERS, 1996, 37 (26) :4525-4528
[55]   Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols [J].
Harada, S ;
Kowase, N ;
Tabuchi, N ;
Taguchi, T ;
Dobashi, Y ;
Dobashi, A ;
Hanzawa, Y .
TETRAHEDRON, 1998, 54 (5-6) :753-766
[56]   Cp2TiCl-mediated selective reduction of α,β-epoxy ketones [J].
Hardouin, C ;
Chevallier, F ;
Rousseau, B ;
Doris, E .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :1046-1048
[57]   CLEAVAGE OF OPTICALLY ACTIVE ALPHA-PHENETHYL PHENYL ETHER WITH HYDROGEN CHLORIDE [J].
HART, H ;
ELIA, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (04) :985-&
[58]   Electron-transfer reactions of aromatic alpha,beta-epoxy ketones: Factors that govern selective conversion to beta-diketones and beta-hydroxy ketones [J].
Hasegawa, E ;
Ishiyama, K ;
Fujita, T ;
Kato, T ;
Abe, T .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2396-2400
[59]   SELECTIVE C(ALPHA)-O BOND-CLEAVAGE OF ALPHA,BETA-EPOXY KETONES TO ALDOLS INDUCED BY FREE-RADICAL PROCESSES [J].
HASEGAWA, E ;
ISHIYAMA, K ;
HORAGUCHI, T ;
SHIMIZU, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (07) :550-552
[60]   EXPLORATORY-STUDY ON PHOTOINDUCED SINGLE ELECTRON-TRANSFER REACTIONS OF ALPHA,BETA-EPOXY KETONES WITH AMINES [J].
HASEGAWA, E ;
ISHIYAMA, K ;
HORAGUCHI, T ;
SHIMIZU, T .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1631-1635