Stereoselective formation of optically active 2-oxy-1, 3-oxazolidin-4-ones and an efficient synthesis of optically active secondary 2-pyrrolidones

Y Omata, A Kakehi, M Shirai, A Kamimura

Index: Omata, Yoji; Kakehi, Akikazu; Shirai, Masashi; Kamimura, Akio Tetrahedron Letters, 2002 , vol. 43, # 39 p. 6911 - 6914

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Citation Number: 10

Abstract

Treatment of (−)-O-acyllactamides or mandelamides with TBSOTf in the presence of base gives optically active 2-oxy-1, 3-oxazolidin-4-ones stereoselectively, which serve as useful precursors for the preparation of optically active secondary 2-pyrrolidones via radical cyclization and subsequent one-step removal of mandelic acid.