Abstract
O-(p-Biphenoyl)-N-tosyl-(L)-allo-threonine methyl ester is synthesized in three steps (65% overall yield) starting from commercially available (L)-allo-threonine methyl ester hydrochloride by N-acylation followed by N,O-acyl migration with inversion of the beta carbinol carbon and N-tosylation. Treatment of the methyl ester with dibromophenylborane gives oxazaborolidinone 1, which can be used as a Lewis acid catalyst for the asymmetric Michael and Diels-Alder reactions.
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