Asymmetric Synthesis and Absolute Configuration of (+)- and (–)-Perhexiline

This work is dedicated to Professor Iwao Ojima on the occasion of his 70^th birthday.

Abstract

Racemic perhexiline has been used (or is currently undergoing clinical trials) for the treatment of a variety of cardiovascular disorders. Increasing evidence suggests that the (–)-enantiomer should be used, as opposed to the racemic mixture. Here, we report the first asymmetric synthesis of both enantiomers of perhexiline in high enantiomeric excess and the assignment of their (–)-S/(+)-R absolute stereochemistry by X-ray crystallography.

Key words

perhexiline - asymmetric synthesis - stereochemistry - medicinal chemistry - crystal structure

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