Strecker氨基酸合成反應(yīng)

氰化鈉，醛酮和胺進(jìn)行縮合得到α-氨基腈，水解得到α-氨基酸的反應(yīng)，稱為Strecker氨基酸合成反應(yīng)。由于氰化鈉毒性太大，而且溶解度不好，常用氰基磷酸二乙酯和丙酮氰醇作為氰源。

反應(yīng)機(jī)理

反應(yīng)實(shí)例

不對稱Strecker反應(yīng)合成硝酮。

Adolph Strecker在160多年前發(fā)現(xiàn)了此反應(yīng)。在它的論文中寫道：“反應(yīng)制備的大塊甘氨酸晶體像珍珠母一樣閃亮，堅(jiān)硬，嚼起來嘎嘣脆?！?P.S. \(^o^)/對自己的純化水平極度自信啊，殘留一點(diǎn)氰化鈉可就掛了。

參考文獻(xiàn)

1. Strecker, A. Ann. 1850, 75, 27-45. Adolph Strecker devised this reaction over 160 years ago. In his paper he described: “The larger crystals of alanine are mother-of-pearl-shiny, hard and crunch between the teeth.”

2. Harusawa, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1979, 20, 4663–4666.

3. Burgos, A.; Herbert, J. M.; Simpson, I. J. Labelled. Compd. Radiopharm. 2000, 43, 891–898.

4. Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762–766.

5. Yet, L. Recent Developments in Catalytic Asymmetric Strecker-Type Reactions, in Organic Synthesis Highlights V, Schmalz, H.-G.; Wirth, T. eds.; Wiley-VCH: Weinheim, Germany, 2003, pp 187-193. (Review).

6. Meyer, U.; Breitling, E.; Bisel, P.; Frahm, A. W. Tetrahedron: Asymmetry 2004, 15, 2029–2037.

7. Huang, J.; Corey, E. J. Org. Lett. 2004, 6, 5027–5029.

8. Cativiela, C.; Lasa, M.; Lopez, P. Tetrahedron: Asymmetry 2005, 16, 2613–2523.

9. Wrobleski, M. L.; Reichard, G. A.; Paliwal, S.; Shah, S.; Tsui, H.-C.; Duffy, R. A.; Lachowicz, J. E.; Morgan, C. A.; Varty, G. B.; Shih, N.-Y. Bioorg. Med. Chem. Lett. 2006, 16, 3859–3863.

10. Galatsis, P. Strecker Amino Acid Synthesis. In Name Reactions for Functional Group Transformations; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2007, pp 477-499. (Review).

11. Belokon, Y. N.; Hunt, J.; North, M. Tetrahedron: Asymmetry 2008, 19, 2804-2815.

12. Sakai, T.; Soeta, T.; Endo, K.; Fujinami, S.; Ukaji, Y. Org. Lett. 2013, 15, 2422–2425.

編譯自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Strecker amino acid synthesis，page 591-592.