Abstract
Diisopropyl allyloxymethylphosphonate prepared by a one‐pot procedure was isomerized to give racemic 1‐hydroxy‐3‐butenylphosphonate with LDA by a [2,3]‐sigmatropic rearrangement. Chloroacetylation delivered an ester, which was resolved in a two‐phase system by using the lipase from Thermomyces lanuginosus. Racemic and (S)‐α‐hydroxyphosphonate 6 were converted to (±)‐ and (R)‐phosphaaspartic acid by functional‐group manipulation. (±)‐, (R)‐ and (S)‐6 were first esterified with 4‐nitrobenzenesulfonyl chloride before hydroboration to transform the double bond into a hydroxyethyl group. The hydroxyl group was manipulated to give a guanidinyl group and the 4‐nitrobenzenesulfonyloxy to give an amino group. Global deprotection of the α‐aminophosphonates yielded the desired phosphaamino acids.
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