Department of Chemistry Indian Institute of Technology Guwahati , Guwahati, Assam 781039, India.
J Org Chem. 2013 Nov 1;78(21):10629-41. doi: 10.1021/jo401450j. Epub 2013 Oct 14.
A simple protocol is described for the synthesis of amido and phenyl hexahydroindolizin-3(2H)-one, hexahydro-1H-quinolizin-4(6H)-one, and 1,3,4,10b-tetrahydropyrido[2,1-a]isoindol-6(2H)-one derivatives via endo-trig (aza-Prins type) cyclization followed by an intermolecular Ritter/Friedel-Crafts reaction of cyclic N-acyliminium ions, which are derived from the boron trifluoride etherate treatment of regioselectively reduced N-homoallyl imides. The reactions are highly diastereoselective with excellent yields.
描述了一种简单的合成酰胺和苯基六氢吲哚啉-3(2H)-酮、六氢-1H-喹啉-4(6H)-酮和 1,3,4,10b-四氢吡啶并[2,1-a]异吲哚-6(2H)-酮衍生物的方法，该方法通过内消旋-三（氮杂-Prins 型）环化反应，随后通过环 N-酰亚胺鎓离子的分子间 Ritter/Friedel-Crafts 反应进行，该离子是通过三氟化硼乙醚处理区域选择性还原的 N-偕亚烯丙基酰亚胺得到的。这些反应具有高度的非对映选择性和优异的收率。
