CHEMISTRY OF DIOXIRANES .27. SOLVENT TUNING OF DIASTEREOSELECTIVITY IN DIMETHYLDIOXIRANE EPOXIDATION REACTIONS

被引：51

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：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 14期

关键词：

D O I：

10.1016/0040-4039(95)00310-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselectivity in the epoxidation of cyclohex-2-en-1-ol shows a remarkable solvent dependence. In some solvent systems the substrate OH group apparently can provide a cis selectivity through H-bonding.

引用

页码：2437 / 2440

页数：4

共 19 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] ADAM W, 1993, TOP CURR CHEM, V164, P45
[4] Adam W., 1992, ORGANIC PEROXIDES, P195
[5] 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
[6] 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
[7] 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
[8] CURCI R, 1990, ADV OXYGENATED PROCE, V2, pCH1
[9] A STRATEGY FOR THE SOLID-PHASE SYNTHESIS OF OLIGOSACCHARIDES
DANISHEFSKY, SJ
MCCLURE, KF
RANDOLPH, JT
RUGGERI, RB
[J]. SCIENCE, 1993, 260 (5112) : 1307 - 1309
[10] STEREOSPECIFIC SYNTHESIS OF ARYL BETA-GLUCOSIDES - AN APPLICATION TO THE SYNTHESIS OF A PROTOTYPE CORRESPONDING TO THE ARYLOXY CARBOHYDRATE DOMAIN OF VANCOMYCIN
DUSHIN, RG
DANISHEFSKY, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (09) : 3471 - 3475

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