REACTION OF DIANION BETA-ENAMINO KETONES WITH ELECTROPHILES .4. SYNTHESIS OF BETA'-HYDROXY-BETA-ENAMINO AND DELTA-HYDROXY-BETA-ENAMINO KETONES

Selective generation techniques of alpha' and gamma dianions of beta-enamino ketones allow an almost complete regiocontrol in the reaction with aldehydes and ketones for the synthesis of beta'- and delta-hydroxy-beta-enamino ketones. An important role is also displayed by bulkiness of the substituent at the nitrogen atom. The reaction gives good to high yields even with enolizable carbonylic compounds. Alpha,beta-insaturated aldehydes and ketones generally undergo 1,2-addition process except in the case of high sterically hindered compounds.