Diastereoselective cyclopropanation via homochiral ketals. Dioxolane structural effects

Eugene A. Mash, Keith A. Nelson, Phillip C. Heidt

Research output: Contribution to journalArticlepeer-review

22 Scopus citations


A series of 2-cyclohexen-1-one ketals related to 2-cyclohexen-1-one 1,4-di- O-benzyl-L-threitol ketal but possesing different dioxolane appendages was prepared and subjected to Simmons-Smith cycloproponation. The observed diastereoselectivity decreased when oxygen was present in the appendages. In the absence of appendage oxygen, the sense of the observed diastereoselectivity was found to depend upon dioxolane chirality. The amount of diastereoselectivity observed was remarkably independent of the nature of the appendages.

Original languageEnglish (US)
Pages (from-to)1865-1868
Number of pages4
JournalTetrahedron Letters
Issue number17
StatePublished - 1987

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


Dive into the research topics of 'Diastereoselective cyclopropanation via homochiral ketals. Dioxolane structural effects'. Together they form a unique fingerprint.

Cite this