posted on 1999-07-16, 00:00authored byStephen Hanessian, Shawn Johnstone
N-t-Butoxycarbonyl-O-sulfonyl-substituted hydroxylamines react with soft enolates to yield O-t-butoxycarbonylamino derivatives rather than the expected Boc-protected amino acids. The reaction
is limited to enolates of β-dicarbonyl compounds. Decarboxylation of the resultant tricarbonyl
compound affords malonyl α-alkyl O-t-butoxycarbonylamino derivatives.