STEREOSELECTIVITY IN THE ALDOL REACTION THE USE OF CHIRAL AND ACHIRAL OXAZOLINES AS THEIR BORON AZENOLATES

Article abstract of DOI:10.1016/0040-4020(84)80014-9

Chiral oxazolines, as their boron enolates derived from various boron triflates, react with aldehydes to give erythro-selectivity (97percent+percent) with enantiomeric purities of 50-60percent.Achiral oxazolines as their boron enolates derived from diisopinocamphenylborane give, on reaction with aldehydes, β-hydroxy esters with high threo-selectivity (90+percent) in 77-85percent ee.A variety of stucturally different oxazolines were also studied and many show high erythro-selectivity.