Polystyrene-supported N-sulfonylated amino alcohols and their applications to titanium(IV) complexes catalyzed enantioselective diethylzinc additions to aldehydes

被引：16

作者：

Hui, Xin-Ping

Chen, Chien-An

Wu, Kuo-Hui

Gau, Han-Mou ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 40202, Taiwan

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHIRALITY | 2007年 / 19卷 / 01期

关键词：

polystyrene-supported catalyst; titanium(IV) complex; N-sulfonylated beta-amino alcohol; diethylzinc; aldehyde; asymmetric ethylation;

D O I：

10.1002/chir.20332

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Crosslinked polystyrene-supported resins 4, 7a, and 7b containing N-sulfonylated beta-amino alcohol in 98, 20, and 40% loadings are prepared. Asymmetric di-ethylzinc additions to benzaldehyde employing titanium complexes of 10 mol % resins 4, 7a, or 7b are examined and the best performed 7a/Ti(O-i-Pr)(4) catalytic system applies to various aldehydes to afford desired secondary alcohols in excellent enantioselectivities up to 95% ee. The resin 7a is reused five times, giving the product with enantioselectivities >= 86% ee and an 81% ee is obtained when the resin is used the sixth time. The used resin 7a is refreshed with 1 M HCl and the asymmetric reaction employing the regenerated resin 7a gives the product in 88% ee.

引用

页码：10 / 15

页数：6

共 61 条

[1] Design of mesoporous aluminosilicates supported (1R,2S)-(-)-ephedrine:: evidence for the main factors influencing catalytic activity in the enantioselective alkylation of benzaldehyde with diethylzinc [J].