Abstract
Playing two roles at once, chiral amines from L-proline or D-mannitol act as protecting groups and as chiral auxiliaries in the [2+2] cycloaddition of formaldehyde hydrazones, such as 1, to ketenes. This strategy, based on the stability of the hydrazones as methanimines and on the development of a new oxidative cleavage of hydrazides, provides a short entry to enantiopure 4-unsubstituted 3-alkoxy- and 3-aminoazetidinones with desired configurations. X=OBn, N(CO2Bn)Bn; Bn=benzyl; MMPP=magnesium monoperoxyphthalate.
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