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

✍ Scribed by Yoji Omata; Akikazu Kakehi; Masashi Shirai; Akio Kamimura

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 74 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01632-5

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✦ Synopsis

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.

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