Selective generation techniques of U' and y dlamons of p-enammo ketones allow an almost complete regmcontrol m the reaction with aldehydes and ketones for the synthesis of p'-and Ghydroxy-P-enammo ketones An Important role IS also &splayed by bulkmess of the substltuent at the nitrogen atom The reachon gives good to high yields even with enollzable carbonyhc compounds c@msaturated aldehydes and ketones generally undergo 1,Zaddmon process except 111 the case of high stencally hmdered compounds 1,3-Dlketones and ther denvatlves are unportant bmldmg blocks for the construcnon of a large vanety of heterocychc compounds1 as well as useful mtermedlates for the synthesis of many blologlcally active molecules 2 The mtroducnon of an alkyl side cham contammg an hydroxyl function at the a'-or y-posmon of a 1,3-dlketone represents an important synthetic goal since the added functionahty would increase the synthetic scope of these mtermedlates However the classical approach le the reaction of 1.3~d~ketone dlamon with aldehydes and ketones suffers of some drawbacks due to an mtrmsic imposslbdlty of reglocontrol m unsymmemcal systems and to very poor yields obtamed with enohzable substrates 3 Analogous unsansfactory results were found when usmg closely related systems such as dlpotasslum or dlsodmm salts of the enammone 4 We have recently shown that m the case of acyclic P-(monoalkylammo)-@unsaturated ketones appropnate generation techniques of the hamon allow an actual reghected control of the attack to CZ'-or 'yposition m the reaction with alkyl halides,5 oxuanes6 and mmles 7 We wsh to report now an application of this procedure to the reactlon with aldehydes and ketones for an efficient and regmcontrolled synthesis of p'and &hydroxy-P-enammo ketones Synthesis of p'-hydroxy+enaminoketones. Treatment of a p-enammo ketone of type lab (see schemes of Tables 1 and 2) with 2 5 equivalent of a strong hthmm base m THF produce both a'-(2) and/ or y-&anion (3) The former product IS the kmencally favoured Isomer bemg, m the mlaally formed monoamon, the yprotons shlelded from attack of the base by the subsatuent at the mtrogen atom Moreover, m the absence of a lithium complexatmg agent the a'-dlamon IS generated m a geometry which does not pemt a rapld mtramolecular lsomensaaon mto the more stable r_isomer 5b Thus, the ophmum con&aons for generation of 2 # for Part 3, see reference 7