N,N-dialkylalloxans -: a new class of catalyst for dioxirane epoxidations

被引:39
作者
Carnell, AJ [1 ]
Johnstone, RAW
Parsey, CC
Sanderson, WR
机构
[1] Univ Liverpool, Robert Robinson Labs, Dept Chem, Liverpool L69 7ZD, Merseyside, England
[2] Solvay Interox Ltd, Warrington WA4 6HB, Cheshire, England
关键词
D O I
10.1016/S0040-4039(99)01610-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N,N-Dimethyl- and N,N-dibenzylalloxans la and Ib have been prepared and used as novel dioxirane catalysts for the epoxidation of a range of di- and tri-substituted alkenes in good to excellent yield. The dibenzylalloxan Ib can be recovered in high yield with no evidence of catalyst decomposition. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8029 / 8032
页数:4
相关论文
共 17 条
[1]   Catalytic enantioselective epoxidation of alkenes with a tropinone-derived chiral ketone [J].
Armstrong, A ;
Hayter, BR .
CHEMICAL COMMUNICATIONS, 1998, (05) :621-622
[2]   Applications of free and resin-bound novel (trifluoromethyl)dioxiranes [J].
Boehlow, TR ;
Buxton, PC ;
Grocock, EL ;
Marples, BA ;
Waddington, VL .
TETRAHEDRON LETTERS, 1998, 39 (13) :1839-1842
[3]  
CLARKLEWIS JW, 1959, J CHEM SOC, P1628
[4]   EPOXIDATION OF ALKENES BY DIOXIRANE INTERMEDIATES GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH KETONES [J].
CURCI, R ;
FIORENTINO, M ;
TROISI, L ;
EDWARDS, JO ;
PATER, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4758-4760
[5]   CATALYTIC EPOXIDATION OF ALKENES WITH OXONE [J].
DENMARK, SE ;
FORBES, DC ;
HAYS, DS ;
DEPUE, JS ;
WILDE, RG .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1391-1407
[6]   Catalytic epoxidation of alkenes with oxone .2. Fluoro ketones [J].
Denmark, SE ;
Wu, ZC ;
Crudden, CM ;
Matsuhashi, H .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8288-8289
[7]   COORDINATION OF CHIRAL AMINES TO COORDINATIVELY UNSATURATED CP-ASTERISK-IR-AMINO ACID COMPLEXES ALLOWS DETERMINATION OF ENANTIOMERIC PURITY [J].
GROTJAHN, DB ;
JOUBRAN, C .
TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :745-752
[8]   ASYMMETRIC HALOLACTIONIZATION REACTION .4. ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ALPHA,BETA-EPOXYALDEHYDES FROM ALPHA,BETA-UNSATURATED ACIDS [J].
HAYASHI, M ;
TERASHIMA, S ;
KOGA, K .
TETRAHEDRON, 1981, 37 (16) :2797-2803
[9]   PHOTOCHEMISTRY OF HETEROCYCLIC COMPOUNDS .2. PHOTOCHEMICAL DECOMPOSITION OF WATER CATALYZED BY ALLOXAN MONOHYDRATE AND ITS DERIVATIVES [J].
OTSUJI, Y ;
WAKE, S ;
IMOTO, E .
TETRAHEDRON, 1970, 26 (17) :4139-&
[10]   A convenient one-pot synthesis of indane-1,2,3-triones by oxidation of indan-1-ones with N-bromosuccinimide-dimethyl sulfoxide reagent [J].
Tatsugi, J ;
Izawa, Y .
SYNTHETIC COMMUNICATIONS, 1998, 28 (05) :859-864