在Olah试剂（HF/pyridine）存在下，α-氨基酸的氨基在重氮化后被氟取代，生成α-氟代羧酸。高HF/pyridine比例(70/30)可能导致重排生成β-氟代羧酸，通常情况下使用的HF/pyridine比例为48/52。α-氨基酸酯也能发生同样的反应。

a.Olah, G, A. Prakas, K, B, S. Chao, Y, L. Hel. Chim. Acta.1981, 64, 2528.

b.Olah, G, A. Welch, J, T. Synthesis. 1974, 65.

c.Olah, G, A. Welch, J, T. J. Org. Chem. 1979,44, 3872.

反应示例：

To the alanine (1.74 g, 20 mmol) in pyridinium polyhydrogen fluoride (50 mL) in polyolefin bottle with good stirring at 0oC was added NaNO2(2.1 g, 30 mmol) in three prortions over aperiod of 30 min. Stirring was continued at room temperature for 5 h, then quenched with 100 mL of ice water and extracted with ether. The organic layer was washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure, the residue was recrystallized to give the desired product (1.39 g, 76%)

【Olah, G, A. Prakas, K, B, S. Chao, Y, L. Hel. Chim. Acta.1981, 64, 2528】

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