DIASTEREOSELECTIVE OXIDATION OF SUBSTITUTED 1,2-DITHIOLAN-3-ONES

被引：11

作者：

GLASS, RS

LIU, YQ

机构：

[1] Department of Chemistry, The University of Arizona, Tucson

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(00)76693-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidation of 1,2-dithiolan-3-ones 1 with one equivalent of dimethyldioxirane in dichloromethane at -78 degrees C produces the corresponding 1,2-dithiolan-3-one 1-oxides 2 in high yield and with diastereoselectivities as high as 18:1. The major diastereomer formed is the trans isomer. An X-ray crystallographic structure study of the major diastereomer 2c obtained by oxidation of 1g is reported.

引用

页码：3887 / 3888

页数：2

共 27 条

[1] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS
ADAM, W
CHAN, YY
CREMER, D
GAUSS, J
SCHEUTZOW, D
SCHINDLER, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) : 2800 - 2803
[2] ALPHA-OXO SULFONES BY DIMETHYLDIOXIRANE OXIDATION OF THIOL ESTERS
ADAM, W
HADJIARAPOGLOU, L
[J]. TETRAHEDRON LETTERS, 1992, 33 (04) : 469 - 470
[3] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS
ADAM, W
CURCI, R
EDWARDS, JO
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) : 205 - 211
[4] STUDIES ON THE REACTION OF 3,3,4,4-TETRAPHENYLTHIETAN-2-ONE
CHARUMILIND, P
KOHN, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (22) : 4359 - 4365
[5] THE REACTIONS OF SULFOXIDES WITH DIMETHYLDIOXIRANE - A QUESTION OF MECHANISM
CLENNAN, EL
YANG, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) : 4504 - 4505
[6] FIELD L, 1973, J MED CHEM, V16, P1152, DOI 10.1021/jm00268a019
[7] HARA M, 1989, J ANTIBIOT, V42, P1768
[8] DC-107, A NOVEL ANTITUMOR ANTIBIOTIC PRODUCED BY A STREPTOMYCES SP
HARA, M
TAKAHASHI, I
YOSHIDA, M
ASANO, K
KAWAMOTO, I
MORIMOTO, M
NAKANO, H
[J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (02) : 333 - 335
[9] DNA STRAND SCISSION BY THE NOVEL ANTITUMOR ANTIBIOTIC LEINAMYCIN
HARA, M
SAITOH, Y
NAKANO, H
[J]. BIOCHEMISTRY, 1990, 29 (24) : 5676 - 5681
[10] HORTMANN AG, 1978, J ORG CHEM, V43, P3374

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