SELECTIVE OXIDATION OF PENICILLIN DERIVATIVES TO PENICILLIN (1R) AND (1S)-SULFOXIDES USING DIMETHYLDIOXIRANE

被引：15

作者：

DANELON, GO ^{[1
]}

MATA, EG ^{[1
]}

MASCARETTI, OA ^{[1
]}

机构：

[1] UNR,FAC CIENCIAS BIOQUIM & FARMACEUT,CONICET,INST QUIM ORGAN SINTESIS,RA-2000 ROSARIO,SANTA FE,ARGENTINA

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(00)61499-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a convenient procedure for preparing (1R)-6,6-dihalo-, 6 beta-halo-penicillanates, 6,6-dihalopenam derivatives and (1S)-6-alpha-halopenicillanates sulfoxides by dimethyldioxirane asymmetric oxidation of the corresponding penicillanates and penam derivatives. This method is characterized by mild reactions conditions, short reaction times, excellent selectivity, very high yield, ease of reaction workup and complete avoidance of overoxidation products.

引用

页码：7877 / 7880

页数：4

共 16 条

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

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

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

[2]

BELINZONI DU, 1988, J CHEM RES-S, P176

[3]

BELINZONI DU, 1988, J CHEM RES-S, P178

[4]

BELINZONI DU, 1988, J CHEM RES M, P1537

[5]

BELINZONI DU, 1988, J CHEM RES M, P1501

[6] CHEMISTRY OF PENICILLANIC ACIDS .I. 6,6-DIBROMO- AND 6,6-DI-IODO-DERIVATIVES [J].

CLAYTON, JP .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (16) :2123-&

[7]

CROSSLEY NS, 1961, TETRAHEDRON LETT, P398

[8] DETERMINATION OF CONFIGURATION OF SOME PENICILLIN S-OXIDES BY C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].

HARRISON, CR ;

HODGE, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (16) :1772-1775

[9]

KAMIYA T, 1973, TETRAHEDRON LETT, P3001

[10] SYNTHESIS OF NEW BETA-LACTAM ANTIBIOTICS [J].

KAMIYA, T ;

TERAJI, T ;

HASHIMOTO, M ;

NAKAGUCHI, O ;

OKU, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (17) :5020-5021

← 1 2 →