三氟甲磺酸铝催化 D-半乳糖醛的串联反应：手性苯并吡喃、色烯和色满的合成。
Aluminum triflate catalyzed tandem reactions of D-galactal: toward chiral benzopyrans, chromenes, and chromans.
机构信息
Research Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg , P.O. Box 524, Auckland Park 2006, South Africa.
出版信息
Org Lett. 2014 Sep 5;16(17):4543-5. doi: 10.1021/ol502305j. Epub 2014 Aug 27.
PMID:25162834
Abstract
3,4,6-Tri-O-acetyl-D-galactal is selectively converted into 1-O-aryl-2-deoxy derivatives or chiral bridged benzopyrans under Al(OTf)3 catalysis, depending on reaction conditions. The benzopyrans react with Al(OTf)3/acetic anhydride in ring-opening reactions in the absence or presence of acetic acid to selectively produce chiral chromenes or chromans, respectively, in high yields.
摘要
在三氟甲磺酸铝（Al(OTf)3）催化下，3,4,6-三-O-乙酰基-D-半乳糖醛可根据反应条件选择性转化为 1-O-芳基-2-脱氧衍生物或手性桥连苯并吡喃。苯并吡喃在无或有乙酸存在下与三氟甲磺酸铝（Al(OTf)3）/乙酸酐进行开环反应，分别以高产率选择性生成手性色烯或色满。
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