A novel chiral auxiliary from chiral spiranes. cis,cis-(+)- and (–)-spiro[4.4]nonane-1,6-diol as chiral modifier in lithium aluminium hydride reduction of phenyl alkyl ketones

Abstract

LiAlH₄ reduction of phenyl alkyl ketones employing the hitherto unexplored chiral auxiliary cis,cis-(+)- and (–)-spiro[4.4]nonane-1,6-diol as chiral modifier gives the corresponding alcohol in 85–90% e.e. (enantiomeric excess).