Abstract

Regioselective opening of the oxirane ring at C(3) of diethyl 2,3-epoxypropylphosphonate 6 with N- or O-benzylhydroxylamine led to 3-( N-benzyl- N-hydroxyamino)- or 3-( N-benzyloxyamino)-2-hydroxypropylphosphonates, 10 or 8. From ( S)- 6 (ee 94%), the phosphonate ( S)- 10 (ee 98%) was prepared in 80% yield. Highly enantiomerically enriched ( R)- and ( S)- 8 (ee 97%) were obtained from ( R)- and ( S)- 6 (ee 88% and 94%), respectively.

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