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
[31]   STUDIES IN STEREOCHEMISTRY .10. THE RULE OF STERIC CONTROL OF ASYMMETRIC INDUCTION IN THE SYNTHESES OF ACYCLIC SYSTEMS [J].
CRAM, DJ ;
ELHAFEZ, FAA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (23) :5828-5835
[32]   OXIDATION OF CHALCONES (AFO REACTION) [J].
CUMMINS, B ;
FLETCHER, H ;
OCINNEIDE, F ;
EADES, JF ;
DONNELLY, DM ;
HEELER, TS ;
WILSON, RK ;
SWIRSKI, J ;
PHILBIN, EM .
TETRAHEDRON, 1963, 19 (04) :499-&
[33]   COURSE OF ALGAR-FLYNN-OYAMADA (AFO) [J].
DEAN, FM ;
PODIMUANG, V .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JUL) :3978-+
[34]   LEWIS ACID-CATALYZED ACYL MIGRATION WITH OPTICALLY-ACTIVE (Z)-1,3-DIPHENYL-2-BUTEN-1-ONE OXIDE AND (E)-1,3-DIPHENYL-2-BUTEN-1-ONE OXIDE - EVIDENCE OF A CONCERTED PATHWAY [J].
DOMAGALA, JM ;
BACH, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (05) :1605-1607
[35]   THE CHEMISTRY OF 2'-AMINO ANALOGS OF 2'-HYDROXYCHALCONE AND ITS DERIVATIVES [J].
DONNELLY, JA ;
FARRELL, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1757-1761
[36]   ALPHA-HALOGENOKETONES .12. EXTENSION OF THE RASODA SYNTHESIS OF DIHYDROFLAVONOLS [J].
DONNELLY, JA ;
FOX, MJ ;
SHARMA, TC .
TETRAHEDRON, 1979, 35 (16) :1987-1991
[37]   SOLVENT MICROSTRUCTURE EFFECT ON REACTION STEREOCHEMISTRY - RING-OPENING OF CHALCONE OXIDES [J].
DURHAM, D ;
KINGSBURY, CA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (07) :923-930
[38]   AN EASY AND EFFICIENT EPOXIDE OPENING TO GIVE HALOHYDRINS USING TIN(II) HALIDES [J].
EINHORN, C ;
LUCHE, JL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (17) :1368-1369
[39]   BIOMIMETIC GERMACRENE-HUMULENE REARRANGEMENT [J].
ENEV, V ;
TSANKOVA, E .
TETRAHEDRON LETTERS, 1988, 29 (15) :1829-1832
[40]   THIOL/DISELENIDE EXCHANGE FOR THE GENERATION OF BENZENESELENOLATE ION - CATALYTIC REDUCTIVE RING-OPENING OF ALPHA,BETA-EPOXY KETONES [J].
ENGMAN, L ;
STERN, D .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5179-5183