Stereoselective Oxidation of an Eleven-Membered Heterocycle
Abstract
Oxidation of macrocyclic phosphine oxide-dithioether 1 produces only the dl form of disulfoxide 2. This selectivity can be rationalized by comparing the crystal structures of starting material and product, and on the basis of VT NMR data, which suggest that the starting macrocycle is conformationally constrained in solution. Molecules containing multiple sulfoxide and/or phosphine oxide groups are of interest as potential hosts for cations and for neutral guests bearing multiple hydrogen bond donors. As part of our exploration of such systems, we have prepared macrocycle 1 and oxidized it to disulfoxide 2. We report here that this oxidation is selective, providing only the dl product; neither of the meso stereoisomers was detected. Structural data for starting material and product suggest that this selectivity results from the conformational preference of eleven-membered ring of 1.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jan 01, 1992
- Accession Number
- ADA252091
Entities
People
- John M. Desper
- Paul B. Savage
- Samuel H. Gellman