Diastereoselective Synthesis of Aliphatic α, α-Difluoro-β3-Amino Esters via a Sonocatalyzed Reformatsky Reaction

TL March, MR Johnston, PJ Duggan

Index: March, Taryn L.; Johnston, Martin R.; Duggan, Peter J. Organic Letters, 2012 , vol. 14, # 1 p. 182 - 185

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Citation Number: 16

Abstract

(R)-2-Phenylglycine ethyl ester was found to be a cheap and effective auxiliary for the preparation of aliphatic α, α-difluoro-β3-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 ...