Enantioselective autocatalysis. III. Configurational and conformational studies on a 1,4-benzodiazepinooxazole derivative

Details Enantioselective autocatalysis. III. Configurational and conformational studies on a 1,4-benzodiazepinooxazole derivative Enantioselective autocatalysis. III. Configurational and conformational studies on a 1,4-benzodiazepinooxazole derivative

Dec 1995

adsabs.harvard.edu/cgi-bin/nph-data_query?bibcode=1995oleb...25..539m&link_type=abstract

Origins of Life and Evolution of the Biosphere, Volume 25, Issue 6, pp.539-547

Physics

1

Scientific paper

We report here on configurational and conformational studies undertaken on the bromofluoro-1,4-benzodiazepinooxazole derivative I, which has previously been found capable of undergoing total spontaneous resolution under racemizing conditions. Due to its bridgehead N-atom I may exist in any of four diastereomeric forms,C r N r (orC s N s ) andC r N s (orC s N r ). Molecular mechanics calculations revealed that in their lowest energy conformations theC r N r (orC s N s ) diastereomers were favored over theC r N s (orC s N r ) diastereomers by some 3.42 kcal/mol, while semi-empirical quantum mechanical calculations indicated heats of formation also favoring theC r N (orC s N s ) diastereomers by 3.83 kcal/mol. The1H NMR spectra of the three crystalline modifications (α, β andγ) of I were examined in acetone, and found to be identical. These data, combined with the results of the above calculations, suggest that I exists in methanol or methanol-acetone solutions as theC r N (orC s N s ) enantiomer prior to its racemization.

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