Tetrahedron

Oxyoxazolidinone as an auxiliary for heterocyclic synthesis. Enantioselective formation of N-unprotected 2-pyrrolidones from selenocarboxylate and allylamines via …

A Kamimura, Y Omata, K Tanaka, M Shirai

Index: Kamimura, Akio; Omata, Yoji; Tanaka, Keiichi; Shirai, Masashi Tetrahedron, 2003 , vol. 59, # 33 p. 6291 - 6299

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Citation Number: 11

Abstract

Optically active N-unprotected 2-pyrrolidones were prepared in a highly stereoselective manner through radical cyclization reaction of oxyoxazolidinone. Asymmetric induction from the oxyoxazolidinone ring system was generally high and oxazabicyclo [3.3. 0] octanones were obtained in good yields. Treatment of the bicyclic compounds with TBAF resulted in the one-step cleavage of C–O and C–N bond, directly giving secondary 2-pyrrolidones in ...

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