Stereoselective sequential photochemical cycloaddition - iminium ion - propargylsilane cyclization. Synthesis of quinolizidines and pyrido [1,2-a]azepines
作者:Lutz F. Tietze、Josef R. Wünsch、Mathias Noltemeyer
DOI:10.1016/s0040-4020(01)88876-1
日期:1992.1
Photochemical cycloaddition of the enaminecarbaldehydes 15 and 16 with the acrylic acid derivatives 20a-c gave the 2-hydroxytetrahydropyridines 21a-c and 24a-c, respectively which cyclize on treatment with trifluoroacetic acid or Lewis acids to furnish the quinolizidines 22a-c and pyrido[1,2-a]azepines 25a-c, respectively in good yields and with high 1,3-induced diastereoselectivity. Indolizidines 27 cannot be prepared by this method.