Using the reaction of the malonate anion with iodovinyl ketone (2) obtained from levoglucosenone (1) t,2 as an example, we suggest a new approach for the construction of the enantiomerically pure functionalized type 3 cyclopropanes that find wide applications in organic synthesis. 3-5
3-1odolevoglucosenone reacts with the sodium derivative of ethyl cyanoacetate at -60 ~ to give a tetrasubstituted eyclopropane derivative; similar reactions of the sodium derivatives of ethyl acetoacetate and acetylacetone at -60 '(2 afford the expected transformed Michael adducts, while at 20 *C, O,C-dialkylated products of the oxetene series are formed.
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