Tetrahedron

Synthetic studies towards proline amide isosteres, potentially useful molecules for biological investigations

Y Takeuchi, A Yamada, T Suzuki, T Koizumi

Index: Takeuchi; Yamada; Suzuki; Koizumi Tetrahedron, 1996 , vol. 52, # 1 p. 225 - 232

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Citation Number: 17

Abstract

2-Ethenylpyrrolidine derivative 8b was prepared from N-protected proline ethyl ester 6b. Bromofluorination of 8b with NBS-Bu4NF/2HF gave a 1: 1 regioisomeric mixture, 9b and 10b (X= Br). Dehydrobromination of 9b and 10b with t-BuOK produced a fluoroolefin 11 and a proline amide isostere model 12, respectively. Deprotection of the Z group in 12 was attempted by treatment with CF3COOH. Although formation of the useful molecule in ...