REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .9. SYNTHESIS AND RING-OPENING REACTIONS OF CIS-OXIDES AND TRANS-OXIDES DERIVED FROM 3-(BENZYLOXYMETHYL)CYCLOPENTENE AND METHYL 2-CYCLOPENTEN-1-CARBOXYLATE

被引：17

作者：

COLOMBINI, M ^{[1
]}

CROTTI, P ^{[1
]}

DIBUSSOLO, V ^{[1
]}

FAVERO, L ^{[1
]}

GARDELLI, C ^{[1
]}

MACCHIA, F ^{[1
]}

PINESCHI, M ^{[1
]}

机构：

[1] UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,I-56126 PISA,ITALY

来源：

TETRAHEDRON | 1995年 / 51卷 / 29期

关键词：

D O I：

10.1016/0040-4020(95)00425-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the oxirane systems derived from cyclopentene bearing a polar functionality (CH(2)OBn or COOMe) in a homoallylic relationship to the oxirane ring. The cis/trans diastereoisomeric epoxide pairs 7-8 and 9-10 derived from 3-(benzyloxymethyl)cyclopentene and methyl 2-cyclopenten-1-carboxylate, respectively, were prepared and some of their opening reactions were studied. The regioselectivity observed turned out to depend on the opening reaction protocol (standard or metal-assisted), suggesting the efficacious incursion, under the appropriate conditions, of chelate bidentate species in the opening process.

引用

页码：8089 / 8112

页数：24

共 25 条

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