Wharton反应

利用肼还原α,β-环氧酮得到烯丙醇的反应。

反应机理

肼和酮反应得到腙,腙然后异构化为二氮烯,进而脱一分子氮气得到产物。

反应实例

反应实例

1. (a) Wharton, P. S.; Bohlen, D. H. J. Org. Chem. 1961, 26, 3615-􀀐3616. (b) Wharton, P. S. J. Org. Chem. 1961, 26, 4781􀀐-4782. Peter S. Wharton earned his Ph.D. at Yale University under the tutelage of Harry H. Wasserman and began his independent academia career at University of Wisconsin at Madison. This was his first paper out of graduate school!【Peter S. Wharton在耶鲁大学Harry H. Wasserman的指导下获得 Ph.D.学位,在威斯康星大学麦迪逊分校进行独立的科研生涯。这篇文章是他毕业后的第一篇论文。】

2. Caine, D. Org. Prep. Proced. Int. 1988, 20, 1-􀀐51. (Review).

3. Dupuy, C.; Luche, J. L. Tetrahedron 1989, 45, 3437-􀀐3444. (Review).

4. Thomas, A. F.; Di Giorgio, R.; Guntern, O. Helv. Chim. Acta 1989, 72, 767-􀀐773.

5. Kim, G.; Chu-Moyer, M. Y.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112,

2003-􀀐2004.

6. Yamada, K.-i.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 3666-􀀐3672.

7. Di Filippo, M.; Fezza, F.; Izzo, I.; De Riccardis, F.; Sodano, G. Eur. J. Org. Chem.2000, 3247􀀐-3249.

8. Takagi, R.; Tojo, K.; Iwata, M.; Ohkata, K. Org. Biomol. Chem. 2005, 3, 2031-􀀐2036.

9. Li, J. J. Wharton Reaction. In Name Reactions for Functional Group Transformations;Li, J. J., Ed.; Wiley: Hoboken, NJ, 2007, pp 152􀀐-158. (Review).

10. Hoye, T. R.; Jeffrey, C. S.; Nelson, D. P. Org. Lett. 2010, 12, 52-􀀐55.

11. Isaka, N.; Tamiya, M.; Hasegawa, A.; Ishiguro, M. Eur. J. Org. Chem. 2012, 665-􀀐668.

编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Wharton reaction,page 626-627.

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