Abstract
Diastereoselection in the synthesis of β-lactams ( 14 and 15) via ketene-imine cycloaddition (Staudinger reaction) using different chiral auxiliaries has been examined. While sterically demanding imines derived from bicyclic aldehyde ( 1) with a β chiral centre provided excellent selectivity, use of imines derived from bicyclic aldehyde ( 17) with a γ chiral centre was not effective. Improvement of stereoselectivity was also sought using imines ( 6 and 7) derived from chiral amines ( 2d,e) and chiral aldehyde ( 1). The bicyclic terpenoid skeleton of the chiral auxiliary in 1 was dismantled by ruthenium tetroxide oxidation to give multiply functionalized β-lactams 23a-d in good yield.
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