The reduction of six α-ketols with different patterns of substitution and size of substituents has been investigated using seven aluminum hydride reagents. The ratio of diastereomeric diols produced was determined by 220-MHz nmr analysis. In each case the predominant diol was the one predicted by Cram's cyclic model. The degree of stereoselectivity correlates well with α-ketol structure with only one reagent (triisobutylaluminum). With the other (agglomerated) reagents, selectivity is related only in an irregular manner to α-ketol structure.
ASJC Scopus subject areas
- Organic Chemistry