Stobbe反应

丁二酸二二甲基及其衍生物和羰基氟化在盐类条件下进行醛的催化。【 Perkin催化 】

催化机理

丁二酸二二甲基先对羰基氟化进行aldol环化，接着构成内酯，强碱拔氢抵消环化获得产物。

催化实例

Stobbe醛后产物醛。

Stobbe产物的关环催化。

连续的Stobbe醛。

注释

1. Stobbe, H. Ber. 1893, 26, 2312. Hans Stobbe (1860-􀀐1938) was born in Tiehenhof, Germany. He earned his Ph.D. In 1889 at the University of Leipzig where he became a professor in 1894.

2. Zerrer, R.; Simchen, G. Synthesis 1992, 922–924.

3. Yvon, B. L.; Datta, P. K.; Le, T. N.; Charlton, J. L. Synthesis 2001, 1556–1560.

4. Liu, J.; Brooks, N. R. Org. Lett. 2002, 4, 3521–3524.

5. Giles, R. G. F.; Green, I. R.; van Eeden, N. Eur. J. Org. Chem. 2004, 4416–4423.

6. Mahajan, V. A.; Shinde, P. D.; Borate, H. B.; Wakharkar, R. D. Tetrahedron Lett. 2005, 46, 1009–1012.

7. Sato, A.; Scott, A.; Asao, T.; Lee, M. J. Org. Chem. 2006, 71, 4692–4695.

8. Kapferer, T.; Brückner, R. Eur. J. Org. Chem. 2006, 2119–2133.

9. Mizufune, H.; Nakamura, M.; Mitsudera, H. Tetrahedron 2006, 62, 8539–8549.

10. Lowell, A. N.; Fennie, M. W.; Kozlowski, M. C. J. Org. Chem. 2008, 73, 1911–1918.

11. Webel, M.; Palmer, A. M.; Scheufler, C.; Haag, D.; Muller, B. Org. Process Res. Dev. 2010, 14, 142􀀐-151.

12. Kodet, J. G.; Wiemer, D. F. J. Org. Chem. 2013, 78, 9291–9302.

编译自： Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Stobbe condensation，page 587-588.