Dakin-West反应

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将α-氨基酸和醋酸酐在碱性条件（吡啶）下反应通过噁唑啉（氨基酸内酯）中间体生成α-乙酰基氨基甲基酮并放出二氧化碳的反应。


反应机理


反应实例



利用杂多酸作为催化剂，乙腈作反应物的绿色Dakin-West反应。


参考文献

1. Dakin, H. D.; West, R. J. Biol. Chem. 1928, 78, 91, 745, and 757. In 1928, Henry Dakin and Rudolf West, a clinician, reported on the reaction of α-amino acids with acetic anhydride to give α-acetamido ketones via azalactone intermediates. Interestingly, one year before this paper by Dakin and West, Levene and Steiger had observed both tyrosine and α-phenylananine gave “abnormal” products when acetylated under these conditions.2,3 Unfortunately, they were slow to identify the products and lost an opportunity to be immortalized by a name reaction.【1928年， Henry Dakin和临床医生Rudolf West报道了α-氨基酸和乙酸酐通过氨基酸内酯中间体得到α-乙酰基氨基酮的反应。有趣的是，早在Dakin和West的论文发表之前一年之前，Levene 和Steiger就观察到络氨酸和α-苯丙氨酸在此条件下乙酰基化会生成一些“奇怪的”产物，但是不幸的是，他们没有很快分离出此产物而错过了被命名反应的机会。】

2. Buchanan, G. L. Chem. Soc. Rev. 1988, 17, 91–109. (Review).

3. Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1997, 62, 1553–1555.

4. Kawase, M.; Hirabayashi, M.; Koiwai, H.; Yamamoto, K.; Miyamae, H. Chem.

Commun. 1998, 641–642.

5. Kawase, M.; Hirabayashi, M.; Saito, S. Recent Res. Dev. Org. Chem. 2001, 4,


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