A novel enzymatic tandem process: utilization of biocatalytic promiscuity for high stereoselective synthesis of 5-hydroxyimino-4,5-dihydrofurans

作者：Wu, Ming-Yu; Li, Kun^*; He, Ting; Feng, Xing-Wen; Wang, Na; Wang, Xiao-Yan; Yu, Xiao-Qi

来源：Tetrahedron, 2011, 67(14): 2681-2688.

DOI：10.1016/j.tet.2011.01.060

• Biocatalytic promiscuity
• Lipase
• Dihydrofuran derivatives
• Tandem reaction
• Water-mediated reaction

A lipase-catalyzed protocol for the synthesis of 5-hydroxyimino-4,5-dihydrofurans via tandem coupling between beta-nitrostyrenes and 1,3-dicarbonyl compounds was developed in a 'one-pot' strategy. A series of beta-nitrostyrenes were employed to expand the scope of this new biocatalytic promiscuity with high stereoselectivity (Z/E up to 99:1) and moderate to good yields. The reaction activity of 1,3-cyclo-hexanedione was found to be better than linear 2,4-pentanedione, while ethyl acetoacetate and diethylmalonate were not suitable for this reaction under the same conditions. Single-crystal X-ray diffraction analysis indicated that the reaction was stereoselective and Z-stereomer was found to be the major product. A reaction mechanism was supposed to elucidate the biocatalytic process.

• 出版日期2011-4-8
• 单位四川大学