Diastereoselectivity in the epoxidation of substituted cyclohexenes by dimethyldioxirane

被引：87

作者：

Murray, RW

Singh, M

Williams, BL

Moncrieff, HM

机构：

[1] Department of Chemistry, University of Missouri - St. Louis, St. Louis

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 05期

关键词：

D O I：

10.1021/jo951864j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three series of compounds based on the cyclohexene framework. have been epoxidized by dimethyldioxirane. A pronounced dependence of epoxide diastereoselectivity on substituent has been observed. In addition there is a solvent influence on this stereoselectivity. The results have been explained by invoking steric, H-bonding, and dipole-dipole influences on the epoxide stereochemistry.

引用

页码：1830 / 1841

页数：12

共 23 条

[1] OXIDATION OF ALLYLIC ALCOHOLS BY DIMETHYLDIOXIRANE - COMPETITION REACTION BETWEEN EPOXIDATION AND C-H INSERTION
ADAM, W
PRECHTL, F
RICHTER, MJ
SMERZ, AK
[J]. TETRAHEDRON LETTERS, 1993, 34 (52) : 8427 - 8430
[2] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS
ADAM, W
CURCI, R
EDWARDS, JO
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) : 205 - 211
[3] [Anonymous], ORGANIC PEROXIDES
[4] KETONE-DIRECTED PERACID EPOXIDATION
ARMSTRONG, A
BARSANTI, PA
CLARKE, PA
WOOD, A
[J]. TETRAHEDRON LETTERS, 1994, 35 (33) : 6155 - 6158
[5] EPOXIDATION OF PRIMARY AND SECONDARY ALKENYLAMMONIUM SALTS WITH DIMETHYLDIOXIRANE, METHYL(TRIFLUOROMETHYL) DIOXIRANE, AND M-CHLOROPERBENZOIC ACID - A GENERAL SYNTHETIC ROUTE TO EPOXYALKYLAMINES
ASENSIO, G
MELLO, R
BOIXBERNARDINI, C
GONZALEZNUNEZ, ME
CASTELLANO, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) : 3692 - 3699
[6] A ROUTE TO ARTIFICIAL GLYCOCONJUGATES AND OLIGOSACCHARIDES VIA ENZYMATICALLY RESOLVED GLYCALS - DRAMATIC EFFECTS OF THE HANDEDNESS OF THE SUGAR DOMAIN UPON THE PROPERTIES OF AN ANTHRACYCLINE DRUG
BERKOWITZ, DB
DANISHEFSKY, SJ
SCHULTE, GK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) : 4518 - 4529
[7] Berti G., 1973, Topics in Stereochemistry, V7, P93
[8] STEREOSPECIFIC VORBRUGGEN-LIKE REACTIONS OF 1,2-ANHYDRO SUGARS - AN ALTERNATIVE ROUTE TO THE SYNTHESIS OF NUCLEOSIDES
CHOW, K
DANISHEFSKY, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) : 4211 - 4214
[9] STEREOSELECTIVITIES AND REGIOSELECTIVITIES IN THE EPOXIDATION OF SOME ALLYLIC ALCOHOLS BY THE DIOXIRANE INTERMEDIATE GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH ACETONE
CICALA, G
CURCI, R
FIORENTINO, M
LARICCHIUTA, O
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) : 2670 - 2673
[10] DIOXIRANE OXIDATIONS - TAMING THE REACTIVITY-SELECTIVITY PRINCIPLE
CURCI, R
DINOI, A
RUBINO, MF
[J]. PURE AND APPLIED CHEMISTRY, 1995, 67 (05) : 811 - 822

← 1 2 3 →