阿赫马托维奇反应

阿赫马托维奇反应是呋喃转变为二氢吡喃环的过程，1971年由小奥斯曼·阿赫马托维奇发现。Synthesis of methyl 2,3-dideoxy--alk-2-enopyranosides from furan compounds : A general approach to the total synthesis of monosaccharides Tetrahedron, Volume 27, Issue 10, 1971, Pages 1973-1996 O. Achmatowicz, P. Bukowski, B. Szechner, Z. Zwierzchowska and A. Zamojski  最初方法是用糠醇与溴在甲醇中反应，先得到2,5-二甲氧基-二氢糠醇，它用稀硫酸发生重排便得到一个二氢吡喃衍生物。该衍生物与原甲酸甲酯和三氟化硼反应上甲基保护基，接着用硼氢化钠还原酮基，可得另一二氢吡喃衍生物，这个产物可用作许多单糖的合成中间体。

600px|阿赫马托维奇反应

这个反应用于天然产物desoxoprosophyllineAsymmetric total synthesis of (+)-desoxoprosophylline Tetrahedron Letters, Volume 39, Issue 50, 10 December 1998, Pages 9227-9228 Cui-Fen Yang, Yi-Ming Xu, Li-Xin Liao and Wei-Shan Zhou  、核球壳菌素（Pyrenophorin）Efficient Conditions for Conversion of 2-Substituted Furans into 4-Oxygenated 2-Enoic Acids and Its Application to Synthesis of (+)-Aspicilin, (+)-Patulolide A, and (-)-Pyrenophorin  Kobayashi, Y.; Nakano, M.; Kumar, G. B.; Kishihara, K. J. Org. Chem.; (Article); 1998; 63(21); 7505-7515.   和包公藤甲素（Bao Gong Teng A）Organometallic Enantiomeric Scaffolding: Organometallic Chirons. Total Synthesis of (-)-Bao Gong Teng A by a Molybdenum-Mediated [5+2] Cycloaddition
Yongqiang Zhang and Lanny S. Liebeskind J. Am. Chem. Soc. 2006; 128(2) pp 465 - 472; (Article)  和全合成中。

最近也用于定向多样性合成 A Synthesis Strategy Yielding Skeletally Diverse Small Molecules Combinatorially 
Martin D. Burke, Eric M. Berger, and Stuart L. Schreiber J. Am. Chem. Soc. 126 (43), 14095 -14104, 2004.   试剂为：NBS、PPTS。另见固相合成。 

600px|阿赫马托维奇Burke 2006

以及 enantiomeric scaffolding 中。Practical, Scalable, High-Throughput Approaches to 3-Pyranyl and 3-Pyridinyl Organometallic Enantiomeric Scaffolds Using the Achmatowicz Reaction Thomas C. Coombs, Maurice D. Lee, IV, Heilam Wong, Matthew Armstrong, Bo Cheng, Wenyong Chen, Alessandro F. Moretto, and Lanny S. Liebeskind J. Org. Chem. 73 (3), 882 -888, 2008. 过程为：氯甲酸苄酯为胺上Cbz保护基；mCPBA促进的阿赫马托维奇反应；与钼的配位。Cp=环戊二烯基。

600px|阿赫马托维奇反应Coombs 2008

参见
化学反应列表

参考资料

Category:杂环合成反应
Category:人名反应