C2-symmetric chiral bis(thiazoline) and bis(oxazoline) ligands and their application in the catalytic asymmetric allylic alkylation

被引：43

作者：

Fu, B ^{[1
]}

Du, DM ^{[1
]}

Xia, Q ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2004年 / 02期

关键词：

bis(thiazolines); bis(oxazolines); synthesis; allylic alkylation; asymmetric catalysis;

D O I：

10.1055/s-2004-815917

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of novel C-2-symmetric bis(thiazoline) ligands with dibenzo[a,c]cycloheptadiene backbone as the substituent on the thiazoline ring were synthesized using the simple reagent phosphorus pentasulfide, and their application in catalytic allylic alkylation was investigated by comparison with the corresponding bis(oxazolines). Palladium-bis(oxazoline) complexes furnished good enantioselectivity (up to 87% ee), while bis(thiazolines) only gave up to moderate enantioselectivity (56% ee) with CH2Cl2 as solvent. Preliminary explanation of the catalysis mechanism is given for the difference of two types of Pd(0)-ligand complexes.

引用

页码：221 / 226

页数：6

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