Highly diastereoselective vinylogous Mukaiyama aldol reaction of α-keto phosphonates with 2-(trimethylsilyloxy)furan catalyzed by Cu(OTf)2.
摘要：
The diastereospecific formation of δ-hydroxyalkylbutenolide phosphonate has been achievedviaa vinylogous Mukaiyama aldol reaction. The reaction was performed using α-ketophosphonate1and 2-(trimethylsilyloxy)furan2mediated by Cu(OTf)2and 2,2,2-trifluoroethanol as additive in CH2Cl2. The reaction proceeds rapidly and affords the corresponding 5-(hydroxy(aryl)methyl) furan-2(5H)-one phosphonates3in 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.
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关键词：
organo‐phosphorus compounds furan derivatives addition reactions diastereoselective syntheses, enantioselective syntheses (incl. cis/trans‐isomerism catalysis, phase‐transfer catalysis
DOI：
10.1039/c1ob05822c
被引量：
年份：
2011
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