Abstract
A variety of optically active 3-substituted-2-azetidinones has been prepared by the annelation of Schiff bases derived from cinnamaldehyde and D-threonine esters and their absolute configuration determined. When the β-hydroxyl group of threonine is unprotected, both enantiomeric forms of N-unsubstituted 3,4-disubstituted-2-azetidinones can be prepared from a single β-lactam-forming reaction. On the other hand, by converting the hydroxyl group of D-threonine to a bulky group (e.g., triphenylsilyl ether), very high diastereoselectivity can be induced. The multiple functional groups on these β-lactams can be easily modified to generate useful synthons for optically active sugars, alkaloids, and monocyclic and bicyclic β-lactam antibiotics.
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