PREPARATION OF PROLINE DERIVED LITHIUM AMIDE BASES AND THEIR USE IN ENANTIOSELECTIVE DEPROTONATION OF MESO EPOXIDES

Article abstract of DOI:10.1016/S0040-4020(01)90297-2

An alternative method of preparation for a range of proline derived chiral lithium amide bases is described. (S)-2-(Pyrrolidinomethyl) pyrrolidine, prepared by the new route, has been used to deprotonate cis and trans ^tbutyldimethylisiloxy-3,4-epoxycyclopentane enantioselectively, thus generating chiral cis and trans ^tbutyldimethylsiloxy-2-cyclopenten-4-ols.The products had higher enantiomeric purity than those produced when the base was prepared by a previously reported method.