Contrasting steric effects of the ketones and aldehydes in the reactions of the diisopinocampheyl enolborinates of methyl ketones with aldehydes

Article abstract of DOI:10.1016/0040-4039(96)00969-0

Treatment of the diisopinocampheylborinates of a representative series of methyl ketones with a representative series of aldehydes, both of differing steric requirements provides aldols whose enantiomeric purifies depend on the steric requirements of both the ketones and the aldehydes. This study has shown that increasing the steric requirements of the R group in the ketones has a pernicious effect on the ee, while increasing the steric requirements of the R group in the aldehydes exerts a beneficial effect on the ee.