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A short, efficient, and highly diastereoselective synthesis of 5-[(1S)-N-Boc-amino-(2S)-(3-fluorophenyl)ethyl]-dihydrofuran-2-one (1) is described. Use of phthalic anhydride as thiolate scavenger effectively preserves the chiral integrity of the α-aminoketone 4 product obtained from the reaction of organozincate 3 with thioester 2.
Aqueous phosphoric acid (85 wt%) is an efficient and mild reagent for the deprotection of N-BOC groups. Acid sensitive functionalities including benzyl and methyl esters, TBDMS ether, CBZ and isopropylidene groups are compatible with the reaction conditions. The reactions are high yielding, and the workup is convenient.
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