Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions
Oskar Popik1, Barbara Grzeszczyk1, Olga Staszewska-Krajewska1
1Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. marek.chmielewski@icho.edu.pl.
Abstract:
Intramolecular Kinugasa reactions on in situ generated carbohydrate-derived alkynylnitrones are described. The effects of the length of chains, their mutual configuration, influence of experimental conditions on product distribution and feasibility of the β-lactam ring construction were studied. Intramolecular reactions proceed with high stereoselectivity to provide in each case one product only. The cycloadducts from tartaric acid were converted into the corresponding non-racemic 4-acetoxy azetidinones in good yields.
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