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

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.

• Publication year

  2018

• Venue

  RSC Advances

• Publication date

  2018-09-18

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1039/c8ra06611fPMID 35547706PMCID 9086373
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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