Synthesis of a Potent hNK-1 Receptor Antagonist via an SN2 Reaction of an Enantiomerically Pure α-Alkoxy Sulfonate

Autor: Nelson, T. D., Rosen, J. D., Smitrovich, J. H., Payack, J., Craig, B., Matty, L., Huffman, M. A., McNamara, J.
Zdroj: Organic Letters; January 2005, Vol. 7 Issue: 1 p55-58, 4p
Abstrakt: The concise synthesis of a stereochemically rich hNK-1 receptor antagonist is described. The synthesis is highlighted by an SN2 reaction of an enantiomerically pure α-alkoxy sulfonate (orthogonally protected butane triol), which was prepared by utilizing salen-mediated hydrolytic kinetic resolution technology. A stereocontrolled acetalization was employed to connect two enantiomerically pure fragments with a high degree of diastereoselectivity.
Databáze: Supplemental Index