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

ABSTRACT: Chiral 3-oxocycloalkanecarbonitriles were prepared by fractional crystallization and crystallization-induced diastereomer transformation (CIDT) of diastereomeric ketals with (1R,2R)-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 (1R,2R)-1,2-diphenylethane-1,2-diol.

SUBMITTER: Yamashita Y

PROVIDER: S-EPMC9086373 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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

Yamashita Yohei Y Maki Daisuke D Sakurai Shiho S Fuse Takumi T Matsumoto Shoji S Akazome Motohiro M

RSC advances 20180921 57

Chiral 3-oxocycloalkanecarbonitriles were prepared by fractional crystallization and crystallization-induced diastereomer transformation (CIDT) of diastereomeric ketals with (1R,2R)-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 yi ...[more]

PMID: 35547706

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