Chan酰氧基乙酸酯重排反应

强碱性条件下，酰氧基乙酸酯经过环氧化物中间体，重排生成2-羟基-3-酮酯的反应。产物可以进一步氧化得到α,β-二酮酯。

氮杂Chan重排反应可以将2,5-二酮基哌嗪重排缩环。

【Dewynter G, Org Biomol Chem, 2008, 6, 3989】

反应实例

2-Hydroxy-3-keto ester (8). To LDA [(from iPr2NH (24 mmol) and n-BuLi (15 mL of 1.6 M in hexane) in dry THF (50 mL), under N2 at 0 C], was added 7 (10 mmol) in THF (10 mL) at -78 C. After 30 min the mixture was quenched with 0.1N HCl, warmed to r.t., worked up and chromatographed to afford 8 (57%).

【Chan TH， Tet Lett， 1984， 25， 3399】

相关文献

1 Chan TH Tet Lett 1984 25 3399

2 Holton RA J Am Chem Soc 1994 116 1597

3 White JD J Org Chem 1996 61 2600

4 Wipf P Org Lett 2001 3 1261

5 Dewynter G Org Biomol Chem 2008 6 3989

6 White JD Tetrahedron 2009 65 6642

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 80。