ENANTIOSELECTIVE OXIDATION OF SULFIDES CATALYZED BY IRON COMPLEXES OF CHIRAL TWIN CORONET PORPHYRINS

被引:61
作者
NARUTA, Y
TANI, F
MARUYAMA, K
机构
[1] Department of Chemistry, Faculty of Science, Kyoto University, Sakyo-ku, Kyoto
关键词
D O I
10.1016/S0957-4166(00)86106-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Ferric porphyrins bearing chiral binaphthalene moieties on their both faces catalyze asymmetric oxidation of sulfides with iodosobenzene as an oxidant in moderate to good optical and chemical yields. Enantiomeric excesses (e.e.) were markedly improved in 2-3 times by the addition of 1-methylimidazole. The mechanism of oxidation and chiral induction are discussed.
引用
收藏
页码:533 / 542
页数:10
相关论文
共 29 条
[1]   BARRIERS TO LINEARITY IN TRIATOMIC MOLECULES .2. COMPARISON OF CURVILINEAR AND RECTILINEAR MODELS AND DETERMINATION OF BARRIERS IN SOME ELECTRONIC STATES OF HYDROGEN SULFIDE, WATER, AND SULFUR-DIOXIDE [J].
BROWN, FB .
JOURNAL OF CHEMICAL PHYSICS, 1973, 58 (03) :827-833
[2]   SHAPE-SELECTIVE OLEFIN EPOXIDATION CATALYZED BY MANGANESE PICNIC BASKET PORPHYRINS [J].
COLLMAN, JP ;
ZHANG, XM ;
HEMBRE, RT ;
BRAUMAN, JI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5356-5357
[3]   H2S+ RADICAL ION - COMPARISON OF PHOTOELECTRON AND OPTICAL SPECTROSCOPY [J].
DIXON, RN ;
DUXBURY, G ;
ROSTAS, J ;
HORANI, M .
MOLECULAR PHYSICS, 1971, 22 (06) :977-&
[4]   ASYMMETRIC HYDROXYLATION BY A CHIRAL IRON PORPHYRIN [J].
GROVES, JT ;
VISKI, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) :8537-8538
[5]   ASYMMETRIC HYDROXYLATION, EPOXIDATION, AND SULFOXIDATION CATALYZED BY VAULTED BINAPHTHYL METALLOPORPHYRINS [J].
GROVES, JT ;
VISKI, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3628-3634
[6]   CATALYTIC ASYMMETRIC EPOXIDATIONS WITH CHIRAL IRON PORPHYRINS [J].
GROVES, JT ;
MYERS, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5791-5796
[7]   CHIRAL SULFOXIDATION BY BIOTRANSFORMATION OF ORGANIC SULFIDES [J].
HOLLAND, HL .
CHEMICAL REVIEWS, 1988, 88 (03) :473-485
[8]   A SHORT ROUTE TO CHIRAL SULFOXIDES USING TITANIUM-MEDIATED ASYMMETRIC OXIDATION [J].
KAGAN, HB ;
DUNACH, E ;
NEMECEK, C ;
PITCHEN, P ;
SAMUEL, O ;
ZHAO, SH .
PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1911-1916
[9]  
LIGHT DR, 1982, BIOCHEMISTRY-US, V21, P2499
[10]   SYNTHESIS OF SULFOXIDES BY OXIDATION OF THIOETHERS [J].
MADESCLAIRE, M .
TETRAHEDRON, 1986, 42 (20) :5459-5495