Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India.
Department of Chemistry, Pt. Neki Ram Sharma Govt. College, Rohtak 124001, India.
J Org Chem. 2020 Jun 5;85(11):7068-7076. doi: 10.1021/acs.joc.0c00432. Epub 2020 May 22.
A route to synthesize 1,2-disubstituted glucals has been developed, which were further converted to substituted chromanes by thermal 6π-electrocyclization in HMPA followed by in situ aromatization. One of the key steps in the synthesis of chromane is metal-free generation of C1-substituted glucal from d-mannose, which was further converted to 1,2-disubstituted glucals by Pd-catalyzed Fujiwara-Moritani reaction with styrenes, acrylates, acrylamide, acrylonitrile, and ethyl vinyl ketone in good yields.
已经开发出了一种合成 1,2-二取代葡萄糖醛的方法，该方法进一步通过在 HMPA 中热 6π-电环化转化为取代的色满，然后进行原位芳构化。色满合成中的关键步骤之一是从 D-甘露糖无金属生成 C1-取代的葡萄糖醛，该葡萄糖醛进一步通过 Pd 催化的 Fujiwara-Moritani 反应与苯乙烯、丙烯酸酯、丙烯酰胺、丙烯腈和乙烯基酮在良好产率下转化为 1,2-二取代葡萄糖醛。
