会用试剂----Burgess试剂

was then removed and quickly replaced with a Teflon cap prior to thereaction being placed into a 50°C bath. After 1 h, the bath temperature wasincreased to 85°C and a small aliquot of the reaction mixture was removed tocheck for the formation of the initial adduct 2(LC/MSgenerally shows M++18(H2O): 426). The reaction was stirred for 12–16 h and thenperiodically monitored, by LC/MS, for the disappearance of 2.(CAUTION: Remove the reaction vessel from the heating bath and allow itstemperature to drop below the boiling point of the solvent prior to removing anytical sample.) Frequently, LC/MS spectra obtained prior towork-up show numerous side products that disappear after work-up. Aftercomplete disappearance of 2, the reaction was cooled to ambienttemperature, benzene was removed in vacuo, and the residue was partitionedbetween EtOAc and 0.5 M HCl. The organic layer was washed with 5% sodiumbicarbonate and brine, then dried over sodium sulfate. Filtration, solventremoval and silica gel chromatography (10–60% EtOAc in hexanes, lineargradient) provided the target compound (318 mg, 77%) as a white solid.

【 Tetrahedron Letters 2002, 3887–3890】

Fredericamycin的制备【Kita, Y. et al. J. Am. Chem. Soc. 2001,123, 3214.】

Taxol的制备【Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597. 】

Penitrem D的制备【Smith, A. B., III et al. J. Am. Chem. Soc. 2003, 125, 8228.】

【Miller, C. P.; Kaufman, D. H. Synlett 2000, 8, 1169–1171.】

Keller, L.; Dumas, F.; D’Angelo, J. Eur. J. Org. Chem. 2003, 2488–2497.

【Nicolaou, K. C.; Snyder, S. A.; Longbottom, D. A.; Nalbandian, A. Z.; Huang, X. Chem. Eur. J. 2004, 10, 5581–5606.】

相关文献

1. Burgess, E. M.; Penton, H.R.; Taylor, E. A. J. Org. Chem.,1973, 38, 26.

2. Creedon, S. M.; Crowley, H. K.; McCarthy, D. G. J. Chem.Soc., Perkin Trans. 1, 1998, 1015.

3. Claremon, D. A.; Phillips, B.T. Tetrahedron Lett., 1988, 29,21552.

4. Maugein, N.; Wagner, A.; Mioskowski, C., Tetrahedron Lett.,1997, 38, 1547.

5. Wipf, P.; Fritch, P. C. Tetrahedron Lett., 1994, 35, 5397.

6. Wipf, P.; Venkatraman, S. Tetrahedron Lett., 1996, 37, 4659.

7. Wipf, P.; Hayes, G. B. Tetrahedron, 1998, 54, 6987.

参考资料

一、Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Burgess dehydrating reagent，page 95-96.

二、解构学空间：%e6%b6%88%e9%99%a4%e5%8f%8d%e5%ba%94/2014/08/post-2566.html

三、 《当代有机制备还原剂——性质、氢解构和反应会》，胡跃飞等所撰

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