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
收藏
页码：1729 / 1734
页数：6
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