Scott D. Kahn

The Effect of Protecting Groups on Chelation Control

Abstract Relative chelating abilities of alcohols, ethers and silyl ethers are rationalized in terms of the π accepting character of the group attached to oxygen. This in turn may be assessed by examination of the bond angle about oxygen.

Diastereofacial selectivity in Diels-Alder cycloadditions involving vinyl sulfoxides

Abstract Diastereofacial selectivities observed for Diels-Alder cycloadditions of achiral dienes with chiral vinyl sulfoxides are rationalized in terms of electrostatics. The “nucleophilic” diene adds to the electron-poor face of the “electrophilic” dienophile.

Conformational analysis of 3-buten-2-ol: A model asymmetric olefin

The conformational energy of 3-buten-2-ol has been investigated using ab initio molecular orbital theory. Six energy minima have been located, the lowest energy two of which are the same as those assigned in a recent microwave study of the molecule. Rationale for the observed preferences are advanced.