HIGHLY REGIOSELECTIVE FORMATION OF BROMOHYDRINS BY REACTION OF EPOXY-AZETIDINONES WITH MGBR2 - AN ALTERNATIVE ROUTE TO 4-BROMOMETHYLCARBONYLMETHYL-2-AZETIDINONE, A KEY CARBAPENEM PRECURSOR

被引：38

作者：

UEDA, Y ^{[1
]}

MAYNARD, SC ^{[1
]}

机构：

[1] BRISTOL MYERS CO LABS,DIV PHARMACEUT RES & DEV,SYRACUSE,NY 13221

来源：

TETRAHEDRON LETTERS | 1988年 / 29卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(00)80715-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

引用

页码：5197 / 5200

页数：4

共 14 条

[1] TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].

CARON, M ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560

[2] NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ACIDS AND AMIDES MEDIATED BY TI(O-I-PR)4 - RELIABLE C-3 SELECTIVITY [J].

CHONG, JM ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1560-1563

[3]

DEVRIES JG, 1985, HETEROCYCLES, V23, P1915

[4] SYNTHESIS OF 3-AMINOALKYL SUBSTITUTED CARBAPENEMS VIA A PHOSPHORANE INTERMEDIATE [J].

DEVRIES, JG ;

SIGMUND, G .

TETRAHEDRON LETTERS, 1985, 26 (23) :2765-2768

[5]

DOWE RD, 1984, TETRAHEDRON LETT, V25, P2061

[6]

FIESER LF, 1967, REAGENTS ORGANIC CHE, V1, P629

[7]

FIESER LF, 1979, REAGENTS ORGANIC SYN, V7, P218

[8] FROM PENICILLIN TO PENEM AND CARBAPENEM .8. INTRODUCTION OF AN ALLYL GROUP AT THE C-4 POSITION OF THE AZETIDINONE MOLECULE, AND THE SYNTHESIS OF DETHIATHIENAMYCIN [J].

FUJIMOTO, K ;

IWANO, Y ;

HIRAI, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (05) :1363-1369

[9] THE REACTION BETWEEN GRIGNARD REAGENTS AND THE OXIRANE RING [J].

GAYLORD, NG ;

BECKER, EI .

CHEMICAL REVIEWS, 1951, 49 (03) :413-533

[10]

HOUSE HO, 1972, MODERN SYNTHETIC REA, P302

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