New homochiral ketoalcohols from aldol reactions of (+)-isomenthone and reversal of diastereoselectivity

Article abstract of DOI:10.1016/S0040-4039(97)10430-0

Aldol reaction of (+)-isomenthone lithium enolate with aryl and alkyl aldehydes proceeds with complete diastereocontrol at the α-carbon (C6), but the stereochemical outcome at the secondary alcohol stereocentre (established by X-ray crystal structure determinations) can be unexpectedly, reversed by changing reaction quenching temperature. This provides a route to a range of new homochiral ketoalcohols.