Stereochemistry of two-phase and substrate-reagent ion-pair reactions of betylates: complete inversion in the synthesis of halogen,sulfur, and nitrogen derivatives from R-(-)-2-octanol

Conversion of a chiral secondary alcohol into a chiral halogen, sulfur or nitrogen derivative may be conveniently carried out by way of a “betylate” ester. The overall reaction gives reasonable (40–40%) yields with high stereoselectivity (100% inversion in seven or eight examples).