利用格氏试剂脱除β-胺基酯的质子进行关环得到β-内酰胺的反应。此反应最早由R. Breckpot在1923年报道。

反应实例

β-Lactam (4). EtMgBr 3 (2 mmol) was added to a stirred solution of 2 (2 mmol) in 5 mL THF (5 mL) at 0 C with stirring under N2. After 2 h the mixture was poured into 20 mL of cold aq NH4Cl. Extraction (ether and DCM), workup and chromatography gave 4 in 91% yield.

【Shibuya M, Heterocycles, 1980, 14 601】

【Schantl JG, Tet Lett, 1987, 28, 6577】

【Naito T, Org Biomol Chem, 2004, 2, 1274】

相关文献

1 Breckport R Bull Soc Chim Belg 1923 32 412

2 Shibuya M Heterocycles 1980 14 601

3 Shono T J Org Chem 1984 49 1056

4 Schantl JG Tet Lett 1987 28 6577

5 Woodward RB Tetrahedron 1993 49 1625

6 Naito T Org Biomol Chem 2004 2 1274

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 61.