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Abstract A simple and an efficient stereoslective synthesis of glycospiroheterocycles has been accomplished via 1, 3-dipolar cycloaddition (1,3-DC) reaction. The azomethine ylide generated by decarboxylative condensation of N-alkylated α-amino acids… Click to show full abstract
Abstract A simple and an efficient stereoslective synthesis of glycospiroheterocycles has been accomplished via 1, 3-dipolar cycloaddition (1,3-DC) reaction. The azomethine ylide generated by decarboxylative condensation of N-alkylated α-amino acids with various diketones was trapped by sugar derived dipolarophiles to give glycospiroheterocycles in good yield (72–94%). All the cycloadducts were well characterized by FT IR, NMR, HRMS and HPLC. The structures were established by 2D NMR. The regio- and stereochemical outcome of some of the cycloadducts were confirmed by a single crystal X-ray analysis. Effect of various solvents on 1, 3 DC reaction was also studied.
Journal Title: Tetrahedron
Year Published: 2020
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