Regioselective and diastereoselective dimethyldioxirane epoxidation of substituted norbornenes and hexamethyl Dewar benzene

被引：7

作者：

Asouti, A ^{[1
]}

Hadjiarapoglou, LP ^{[1
]}

机构：

[1] Univ Ioannina, Dept Chem, Sect Organ Chem & Biochem, GR-45110 Ioannina, Greece

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 04期

关键词：

dimethyldioxirane; epoxidation; diastereoselectivity; regioselectivity; substituted norbornenes;

D O I：

10.1016/S0040-4039(99)02113-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various substituted norbornenes, such as endo-dicyclopentadiene 1, exo-dicyclopentadiene 5, 5-methylenebicyclo[2.2.1]hept-2-ene 8 and hexamethyl Dewar benzene 10 were transformed into the corresponding mono- and bis-epoxides by epoxidation with dimethyldioxirane (as an acetone solution). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：539 / 542

页数：4

共 30 条

[1] Enantioselective oxidation of vic-diols to optically active α-hydroxy ketones by a fructose-derived dioxirane [J].

Adam, W ;

Saha-Möller, CR ;

Zhao, CG .

TETRAHEDRON-ASYMMETRY, 1998, 9 (23) :4117-4122

[2]

Adam W, 1996, B SOC CHIM BELG, V105, P581

[3] DIMETHYLDIOXIRANE EPOXIDATION OF 6,6-DISUBSTITUTED FULVENES [J].

ADAM, W ;

HADJIARAPOGLOU, LP ;

MEFFERT, A .

TETRAHEDRON LETTERS, 1991, 32 (46) :6697-6700

[4] Synthesis of optically active α-hydroxy ketones by enantioselective oxidation of silyl enol ethers with a fructose-derived dioxirane [J].

Adam, W ;

Fell, RT ;

Saha-Möller, CR ;

Zhao, CG .

TETRAHEDRON-ASYMMETRY, 1998, 9 (03) :397-401

[5] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211

[6]

ADAM W, 1993, TOP CURR CHEM, V164, P45

[7]

[Anonymous], ORGANIC PEROXIDES

[8] THE ENDO TO EXO ISOMERIZATION OF DICYCLOPENTADIENE [J].

BAKKE, JM ;

LUNDQUIST, M .

ACTA CHEMICA SCANDINAVICA, 1990, 44 (08) :860-861

[9]

CLENNAN EL, 1995, TRENDS ORG CHEM, V5, P231

[10]

CURCI R, 1980, ADV OXYGENATED PROCE, V2, P1

← 1 2 3 →