KETONE-DIRECTED PERACID EPOXIDATION

被引：11

作者：

ARMSTRONG, A ^{[1
]}

BARSANTI, PA ^{[1
]}

CLARKE, PA ^{[1
]}

WOOD, A ^{[1
]}

机构：

[1] PFIZER LTD,CENT RES,SANDWICH CT13 9NJ,KENT,ENGLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 33期

关键词：

D O I：

10.1016/0040-4039(94)88103-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ketone carbonyl groups are shown to direct the epoxidation of cyclic alkenes with higher selectivity than that displayed by esters. An O-18 labelling study is used to show that a dioxirane intermediate is not involved in these reactions.

引用

页码：6155 / 6158

页数：4

共 21 条

[1] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS
ADAM, W
CURCI, R
EDWARDS, JO
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) : 205 - 211
[2] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE
ADAM, W
BIALAS, J
HADJIARAPOGLOU, L
[J]. CHEMISCHE BERICHTE, 1991, 124 (10) : 2377 - 2377
[3] IMPROVED STEREOCONTROLLED SYNTHESIS OF THREO PEPTIDYL EPOXIDES
ALBECK, A
PERSKY, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) : 653 - 657
[4] IODOTRIMETHYLSILANE-PROMOTED ADDITIONS OF MONOORGANOCOPPER COMPOUNDS TO ALPHA,BETA-UNSATURATED KETONES, ESTERS, AND LACTONES
BERGDAHL, M
ERIKSSON, M
NILSSON, M
OLSSON, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) : 7238 - 7244
[5] ON STEROIDS .337. A CONTRIBUTION TO PEROXY ACID OXIDATION OF ALPHA, BETA-UNSATURATED KETONES AND LINEARLY CONJUGATED DIENONES - REACTIONS IN THE CHOLESTANE SERIES
CERNY, V
BUDESINSKY, M
RYBA, M
TURECEK, F
[J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1988, 53 (07) : 1549 - 1567
[6] EPOXIDATION OF ALLYLIC ALCOHOLS WITH PEROXY-ACIDS - ATTEMPTS TO DEFINE TRANSITION STATE GEOMETRY
CHAMBERL.P
ROBERTS, ML
WHITHAM, GH
[J]. JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (07): : 1374 - &
[7] ASPECTS OF STEREOCHEMISTRY .1. STEREOSPECIFICITY IN FORMATION OF EPOXIDES FROM CYCLIC ALLYLIC ALCOHOLS
HENBEST, HB
WILSON, RAL
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1957, (MAY): : 1958 - 1965
[8] ALLYLIC 1,3-STRAIN AS A CONTROLLING FACTOR IN STEREOSELECTIVE TRANSFORMATIONS
HOFFMANN, RW
[J]. CHEMICAL REVIEWS, 1989, 89 (08) : 1841 - 1860
[9] SUBSTRATE-DIRECTABLE CHEMICAL-REACTIONS
HOVEYDA, AH
EVANS, DA
FU, GC
[J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1307 - 1370
[10] STEREOSELECTIVE EPOXIDATION OF PHE-GLY AND PHE-PHE VINYL ISOSTERES
JENMALM, A
BERTS, W
LI, YL
LUTHMAN, K
CSOREGH, I
HACKSELL, U
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) : 1139 - 1148

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