Rhodium(II) Acetate Catalyzed Synthesis of Cyclic Enamides and Enamines via β-Hydride Elimination

Abstract

A series of cylic diazoamides and diazoamines were synthesized. Treatment of these cylic diazoamides and diazoamines with a catalytic amount of rhodium(II) acetate furnished the corresponding cyclic enamides and enamines, respectively. Interestingly, cyclic diazoamines produced stereoselectively Z-enamines.

Key words

diazoamides - diazoamines - enamides - enamines - rhodium(II) acetate

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11

¹H NMR spectra showed no trace of the E-isomer in the crude reaction mixtures of 4d-f even before chromatography.