CONCISE STEREOSELECTIVE SYNTHESIS OF 1-PERFLUOROALKYL ENAMINES VIA THE ADDITION OF N-LITHIATED AMINES TO ENOL ETHERS AND THEIR SUBSEQUENT METALATION TO FORM NEW FUNCTIONALIZED ENAMINES

Addition of lithium amides derived from a range of cyclic, sterically demanding, and chiral amines, to trifluoromethyl (Z)-enol ethers 1 and 4, provides stereoselectively the corresponding (Z)-enamines 3a-e and 7 in good yields. This reaction has been extended to the perfluoroalk yl and chlorofluoroalkyl enol ethers (CF2Cl, C2F5). The enamines can r eact with (BuLi)-Li-t to give vinylic anions and, after quenching with aldehydes and ethyl chloroformate, provide new functionalized enamine s 12-16.