Dicobalt octacarbonyl promoted rearrangement of 4-isoxazolines to acylaziridines: Dramatic rate acceleration with very high substrate tolerance

被引：59

作者：

Ishikawa, T ^{[1
]}

Kudoh, T ^{[1
]}

Yoshida, J ^{[1
]}

Yasuhara, A ^{[1
]}

Manabe, S ^{[1
]}

Saito, S ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Biosci & Biotechnol, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 11期

关键词：

D O I：

10.1021/ol025906j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Dicobalt octacarbonyl [CO2(CO)(8)] in acetonitrile at 75 degreesC triggers the cleavage of the N-O bond of 4-isoxazolines (1) to bring about the valence rearrangement to 2-acylaziridines (2). The isoxazolines were stable at 75 degreesC in the absence of the cobalt complex.

引用

页码：1907 / 1910

页数：4

共 29 条

[1] THE MECHANISM OF SUBSTITUTION OF DICOBALT OCTACARBONYL [J].

ABSIHALABI, M ;

ATWOOD, JD ;

FORBUS, NP ;

BROWN, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (20) :6248-6254

[2]

Antilla JC, 2000, ANGEW CHEM INT EDIT, V39, P4518

[3] Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction [J].

Aschwanden, P ;

Frantz, DE ;

Carreira, EM .

ORGANIC LETTERS, 2000, 2 (15) :2331-2333

[4] VALENCE REARRANGEMENT OF HETERO SYSTEMS - 4-ISOXAZOLINES [J].

BALDWIN, JE ;

PUDUSSER.RG ;

QURESHI, AK ;

SKLARZ, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (19) :5325-&

[5]

CALLE L, 1994, J CHEM SOC CHEM COMM, P301

[6] N,O-HETEROCYCLICS .11. SKELETAL REARRANGEMENT OF N,O-HETEROCYCLES - ISOXAZOLINONE TO AZIRIDINE TRANSFORMATION INDUCED BY LITHIUM ALUMINUM-HYDRIDE [J].

CHIDICHIMO, G ;

CUM, G ;

LELJ, F ;

SINDONA, G ;

UCCELLA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (04) :1372-1377

[7] NEW SYNTHESIS OF ETHYL 2,3-DIHYDRO-1H-PYRROLO[1,2-A]INDOLE-9-CARBOXYLATES VIA APPARENT 1-AZA-1'-OXA [3,3]SIGMATROPIC REARRANGEMENT [J].

COATES, RM ;

HUTCHINS, CW .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (25) :4742-4744

[8]

COLLMAN JP, 1987, PRINCIPLES APPL ORGA, P266

[9] Copper-catalyzed nitrogen transfer mediated by iodosylbenzene PhI=O [J].

Dauban, P ;

Sanière, L ;

Tarrade, A ;

Dodd, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7707-7708

[10] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].

EVANS, DA ;

WOERPEL, KA ;

HINMAN, MM ;

FAUL, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728

← 1 2 3 →