ENANTIOSELECTIVE ALLYLIC OXIDATION CATALYZED BY CHIRAL BISOXAZOLINE-COPPER COMPLEXES

被引：155

作者：

GOKHALE, AS

MINIDIS, ABE

PFALTZ, A

机构：

[1] UNIV BASEL,INST ORGAN CHEM,CH-4056 BASEL,SWITZERLAND

[2] UNIV BASEL,INST PHARMAZEUT,CH-4051 BASEL,SWITZERLAND

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 11期

关键词：

D O I：

10.1016/0040-4039(95)00140-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(I) complexes prepared in situ rom chiral bisoxazolines and Cu(I)OTf have been studied as catalysts for the allylic oxidation of cycloalkenes, Using 5 mol% of catalyst and tert-butyl perbenzoate as oxidant, optically active 2-cycloalkenyl benzoates were obtained in moderate to good yields. The highest enantiomeric excesses, 74% at 23 degrees C and up to 84% at lower temperatures, were observed for cyclopentene and cycloheptene, while cyclohexene gave somewhat lower selectivities ranging between 64-77%ee,

引用

页码：1831 / 1834

页数：4

共 41 条

[1]

ANDRUS M, COMMUNICATION

[2]

[Anonymous], 1992, ANGEW CHEM, V104, P439

[3]

ARAKI M, 1976, Patent No. 2625030

[4] ASYMMETRIC TRANSFORMATION OF SYMMETRICAL EPOXIDES TO ALLYLIC ALCOHOLS BY LITHIUM (S)-2-(N,N-DISUBSTITUTED AMINOMETHYL)PYRROLIDIDE [J].