Journal of Organic Chemistry 2008-10-03

Structural and spatial considerations in the N,N'-diacyl- and bis(alkoxycarbonyl)bispidinone series.

Shlomo Levinger, Yifat Sharabi-Ronen, Alexander Mainfeld, Amnon Albeck

Index: J. Org. Chem. 73(19) , 7793-6, (2008)

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Abstract

Diamidic and dicarbamic bispidinones show trans-cis isomerism, the relative population in solution of the cis form increasing with solvent polarity. The mutual proximity of the two amide functions in 4a has no impact on the barrier to isomerization. The system represents a peculiar case of planar chirality posing a challenge to its specification.