Abstract
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 language | English (US) |
|---|---|
| Pages (from-to) | 1865-1868 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 28 |
| Issue number | 17 |
| DOIs | |
| State | Published - 1987 |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Mash, E. A., Nelson, K. A., & Heidt, P. C. (1987). Diastereoselective cyclopropanation via homochiral ketals. Dioxolane structural effects. Tetrahedron Letters, 28(17), 1865-1868. https://doi.org/10.1016/S0040-4039(00)95995-1