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Chiral 3-oxocycloalkanecarbonitriles were prepared by fractional crystallization and crystallization-induced diastereomer transformation (CIDT) of diastereomeric ketals with (1 R ,2 R )-1,2-diphenylethane-1,2-diol. Investigation of the crystal structures by X-ray diffraction analysis revealed that the difference in hydrogen bonds caused the discrepancy of the solubilities between ( R ) and ( S ) diastereomers. Furthermore, CIDT to afford the ( R )-diastereomer in good yield (95% yield) and with high diastereoselectivity (97% de) was accomplished, which is the first example of CIDT of neutral compounds via formation of the diastereomeric ketal with (1 R ,2 R )-1,2-diphenylethane-1,2-diol.

rsc advances

Preparation of chiral 3-oxocycloalkanecarbonitrile and its derivatives by crystallization-induced diastereomer transformation of ketals with chiral 1,2-diphenylethane-1,2-diol