Tetrahedron

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

MY Wu, K Li, T He, XW Feng, N Wang, XY Wang…

Index: Wu, Ming-Yu; Li, Kun; He, Ting; Feng, Xing-Wen; Wang, Na; Wang, Xiao-Yan; Yu, Xiao-Qi Tetrahedron, 2011 , vol. 67, # 14 p. 2681 - 2688

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Citation Number: 21

Abstract

A lipase-catalyzed protocol for the synthesis of 5-hydroxyimino-4, 5-dihydrofurans via tandem coupling between β-nitrostyrenes and 1, 3-dicarbonyl compounds was developed in a 'one-pot'strategy. A series of β-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-cyclohexanedione was found to be better than ...