engleski

Diels-Alder reactions on imines derived from 3-amino-β -lactams

Synthesis of diversily substituted monocyclic β -lactams have been of considerable interest to the synthetic community in the past few decades. Because of the recent developments using β -lactams as synthons for several biologically active compounds, research on this topic has gained tremendous attention. Hetero Diels- Alder reactions involving imino-dienes or imino-dienophiles are widely used for the construction of nitrogen-containing compounds. Our interest in the use of 3-amino-β -lactams as starting substrates for the preparation of potentially bioactive products prompted us to evaluate the combination of the aza-Diels- Alder reaction of 2-azetidinone-tethered imines with siloxydienes as a route to the asymmetric synthesis of 5, 6-dihydro-g-pyridones using b-lactams as chiral building blocks. Effects of various dienes and substituents on dienophile, Lewis acids, and solvents on the product formation and diastereoselectivity of the reactions will be discussed.

Diels-Alder reactions; 3-amino-β -lactams

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