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Diastereoselective synthesis of aliphatic α,α-difluoro-β3-amino esters via a sonocatalyzed Reformatsky reaction

Diastereoselective synthesis of aliphatic α,α-difluoro-β3-amino esters via a sonocatalyzed Reformatsky reaction

Organic Letters 14(1): 182-185

(R)-2-Phenylglycine ethyl ester was found to be a cheap and effective auxiliary for the preparation of aliphatic α,α-difluoro-β(3)-amino esters via a Reformatsky reaction performed under sonication conditions. The products were obtained in good to high yield and ≥96:4 dr, thus providing a new stereoselective route to this under-represented class of compounds. A facile one-pot removal of the phenylglycine moiety and concomitant Boc protection subsequently afforded the corresponding Boc-protected β(3)-amino esters in excellent yield.

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Accession: 052591875

Download citation: RISBibTeXText

PMID: 22121827

DOI: 10.1021/ol202969w

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