EFFECT DE SOLVANT REMARQUABLE DANS L'ADDITION DIASTEREOSELECTIVE D'ORGANOCUPRATES SUR UNE OXAZOLIDINE CHIRALE α,β INSATUREE

Article abstract of DOI:10.1016/S0022-328X(00)98841-7

In diastereoselective addition of methylcopper and dimethylcuprate to a chiral α-β-ethylenic oxazolidine in Et2O or THF, 3-(S)-phenylbutanal is formed with (ee) in the range of 30 to 50percent.Use of apolar solvents like hexane gives an inversion of configuration and an increase of the enantiomeric excess up to 80percent.