Organocatalytic Highly Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates

被引：41

作者：

Perera, Sandun ^{[2
]}

Naganaboina, Vijaya Kumar ^{[2
]}

Wang, Long ^{[1
]}

Zhang, Bin ^{[1
]}

Guo, Qunsheng ^{[2
]}

Rout, Laxmidhar ^{[2
]}

Zhao, Cong-Gui ^{[2
]}

机构：

[1] Univ Texas Hlth Sci Ctr San Antonio, Dept Med, San Antonio, TX 78229 USA

[2] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 10期

关键词：

aldehydes; hydroxyphosphonates; ketophosphonates; organocatalysis; primary amines; DIRECT ALDOL REACTION; HYDROXY PHOSPHONATES; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; ALPHA; BETA-UNSATURATED KETONES; NITROALDOL REACTION; MANNICH REACTIONS; ACETALDEHYDE; DERIVATIVES; INHIBITORS;

D O I：

10.1002/adsc.201000835

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The cross-aldol reaction between enolizable aldehydes and alpha-ketophosphonates was achieved for the first time by using 9-amino-9-deoxy-epi-quinine as the catalyst. beta-Formyl-alpha-hydroxyphosphonates were obtained in high to excellent enantioselectivities. The reaction works especially well with acetaldehyde, which is a tough substrate for organocatalyzed cross-aldol reactions. The products were demonstrated to have anticancer activities.

引用

页码：1729 / 1734

页数：6

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