Synthesis of novel chiral bisoxazoline ligands containing 2,5-diaryl-1,3,4-oxadiazole and enantioselective cyclopropanation of styrene

被引：15

作者：

Du, DM ^{[1
]}

Wang, ZY ^{[1
]}

Xu, DC ^{[1
]}

Hua, WT ^{[1
]}

机构：

[1] Peking Univ, Coll Chem & Mol Engn, Key Lab Biooorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2002年 / 16期

关键词：

bisoxazoline; oxadiazole; enantioselective cyclopropanation;

D O I：

10.1055/s-2002-35232

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Practical synthesis of chiral C-2-symmetric substituted bisoxazoline ligands containing 2,5-diaryl-1,3,4-oxadiazole units was investigated. Five chiral bisoxazoline ligands containing 2,5-diphenyl-1,3,4-oxadiazole have been synthesized from 2,5-di-(o-carboxylphenyl)-1,3,4-oxadiazole and amino alcohols by methanesulfonyl chloride or p-toluenesulfonyl chloride assisted cyclization via hydroxy amide intermediate. Preliminary examination of copper complexes of new ligands as chiral catalysts in the enantioselective cyclopropanation of styrene with ethyl diazoacetate was performed. Enantioselectivities up to 35% ee and 87% ee for trans- and cis-2-phenylcyclopropanecarboxyl ate, respectively were observed.

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页码：2347 / 2352

页数：6

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