RUTHENIUM-CATALYZED OXIDATION OF BETA-LACTAMS WITH MOLECULAR-OXYGEN AND ALDEHYDES

被引：71

作者：

MURAHASHI, SI ^{[1
]}

SAITO, T ^{[1
]}

NAOTA, T ^{[1
]}

KUMOBAYASHI, H ^{[1
]}

AKUTAGAWA, S ^{[1
]}

机构：

[1] TAKASAGO RES INST INC,KAMATA,TOKYO 144,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 42期

关键词：

OXIDATION OF BETA-LACTAMS; 4-ACYLOXY BETA-LACTAMS; RUTHENIUM CATALYST; AEROBIC OXIDATION; OXORUTHENIUM SPECIES;

D O I：

10.1016/S0040-4039(00)79446-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The RuCl3 catalyzed reaction of beta-lactams in the presence of acetaldehyde and molecular oxygen in an acid and ethyl acetate under buffer conditions gives the corresponding 4-acyloxy beta-lactams highly efficiently.

引用

页码：5991 / 5994

页数：4

共 16 条

[1]

BOULLION G, 1983, CHEM PEROXIDES, P297

[2] SYNTHESIS OF 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATES INVOLVING THE LABILE ACYL AUXILIARY 4,4-DIMETHYL-1,3-OXAZOLIDINE-2-THIONE [J].

DEZIEL, R ;

FAVREAU, D .

TETRAHEDRON LETTERS, 1989, 30 (11) :1345-1348

[3] LEWIS ACID MEDIATED CONDENSATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF CHIRAL CARBAPENEM PRECURSORS [J].

FUENTES, LM ;

SHINKAI, I ;

SALZMANN, TN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4675-4676

[4] A HIGHLY STEREOSELECTIVE SYNTHESIS OF A KEY INTERMEDIATE OF 1-BETA-METHYLCARBAPENEMS EMPLOYING THE REFORMATSKY REACTION OF 3-(2-BROMOPROPIONYL)-2-OXAZOLIDONE DERIVATIVES [J].

ITO, Y ;

TERASHIMA, S .

TETRAHEDRON LETTERS, 1987, 28 (52) :6625-6628

[5] RUTHENIUM-CATALYZED OXIDATIVE CLEAVAGE REACTION OF CARBON-CARBON DOUBLE-BONDS USING MOLECULAR-OXYGEN [J].

KANEDA, K ;

HARUNA, S ;

IMANAKA, T ;

KAWAMOTO, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (21) :1467-1468

[6] HIGHLY STEREOSELECTIVE ASYMMETRIC HYDROGENATION OF 2-BENZAMIDOMETHYL-3-OXOBUTANOATE CATALYZED BY CATIONIC BINAP RUTHENIUM(II) COMPLEXES [J].

MASHIMA, K ;

MATSUMURA, Y ;

KUSANO, K ;

KUMOBAYASHI, H ;

SAYO, N ;

HORI, Y ;

ISHIZAKI, T ;

AKUTAGAWA, S ;

TAKAYA, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (09) :609-610

[7] RUTHENIUM-CATALYZED CYTOCHROME-P-450 TYPE OXIDATION OF TERTIARY-AMINES WITH ALKYL HYDROPEROXIDES [J].

MURAHASHI, S ;

NAOTA, T ;

YONEMURA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8256-8258

[8] RUTHENIUM-CATALYZED OXIDATION OF AMIDES AND LACTAMS WITH PEROXIDES [J].

MURAHASHI, SI ;

NAOTA, T ;

KUWABARA, T ;

SAITO, T ;

KUMOBAYASHI, H ;

AKUTAGAWA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) :7820-7822

[9] ASYMMETRIC TOTAL SYNTHESIS OF A NEW NON-NATURAL 1-BETA-METHOXYCARBAPENEM [J].

NAGAO, Y ;

ABE, T ;

SHIMIZU, H ;

KUMAGAI, T ;

INOUE, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (13) :821-823

[10] STEREOSELECTIVE HYDROGENATION VIA DYNAMIC KINETIC RESOLUTION [J].

NOYORI, R ;

IKEDA, T ;

OHKUMA, T ;

WIDHALM, M ;

KITAMURA, M ;

TAKAYA, H ;

AKUTAGAWA, S ;

SAYO, N ;

SAITO, T ;

TAKETOMI, T ;

KUMOBAYASHI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (25) :9134-9135

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