Synthesis of functionalized allylic sulfoxides and their use in the construction of 2, 3, 4-trisubstituted furans via a [3+ 2] annulation

Z Fu, M Wang, Y Ma, Q Liu, J Liu

Index: Fu, Zhenqian; Wang, Mang; Ma, Yuhui; Liu, Qun; Liu, Jun Journal of Organic Chemistry, 2008 , vol. 73, # 19 p. 7625 - 7630

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Citation Number: 26

Abstract

A route to 2, 3, 4-trisubstituted furan derivatives based on a [3+ 2] annulation of functionalized allylic sulfoxides and aldehydes is described. In this strategy, the precursors of allylic sulfoxides 4, allylic sulfides 3, were synthesized via a thiomethylation reaction of an α-EWG ketene-S, S-acetal 1 (EWG: electron-withdrawing group), formaldehyde, and a thiol 2 in high to excellent yields. Allylic sulfoxides 4 were prepared by a highly regioselective ...