ENANTIOSELECTIVE ALLYLIC OXIDATION CATALYZED BY CHIRAL BISOXAZOLINE-COPPER COMPLEXES

ENANTIOSELECTIVE ALLYLIC OXIDATION CATALYZED BY CHIRAL BISOXAZOLINE-COPPER COMPLEXES
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DOI:
10.1016/0040-4039(95)00140-8
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发表时间:
1995-03-13
影响因子:
1.8
通讯作者:
PFALTZ, A
PFALTZ, A
中科院分区:
化学4区
文献类型:
--
作者:
GOKHALE, AS;MINIDIS, ABE;PFALTZ, A

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本文研究了由手性双恶唑啉和Cu(I)OTf原位合成的Cu(I)配合物催化环烯烃烯丙基氧化反应。在5mol%的催化剂和过苯甲酸叔丁酯作氧化剂下,以中等至良好的产率得到了光学活性的2-环烯基苯甲酸酯。对于环戊烯和环庚烯,观察到最高的对映体过量,在23 ° C下为74%,在较低温度下高达84%,而环己烯的选择性稍低,在64-77%ee之间,
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,