Highly diastereoselective vinylogous Mukaiyama aldol reaction of α-keto phosphonates with 2-(trimethylsilyloxy)furan catalyzed by Cu(OTf)2

被引：11
|
作者：
Yu, Jipan
Zhao, Xiaona
Miao, Zhiwei [1 ]
Chen, Ruyu
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 19期
基金：
中国国家自然科学基金;
关键词：
ENANTIOSELECTIVE SYNTHESIS; ENOL ETHERS; INHIBITORS; DERIVATIVES;
D O I：
10.1039/c1ob05822c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The diastereospecific formation of delta-hydroxyalkylbutenolide phosphonate has been achieved via a vinylogous Mukaiyama aldol reaction. The reaction was performed using alpha-ketophosphonate 1 and 2-(trimethylsilyloxy)furan 2 mediated by Cu(OTf)(2) and 2,2,2-trifluoroethanol as additive in CH2Cl2. The reaction proceeds rapidly and affords the corresponding 5-(hydroxy(aryl)methyl)furan-2(5H)-one phosphonates 3 in high yields with good to excellent diastereoselectivities (d.r. up to > 99 : 1). 5-(Hydroxy(alkyl)methyl)furan-2(5H)-one phosphonates could also be obtained with good diastereoselectivities.
引用
收藏
页码：6721 / 6726
页数：6
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