Regio- and Stereoselective Hydrosulfonylation of Electron-Deficient Alkynes: Access to Both E- and Z-β-Sulfonyl-α,β-Unsaturated Carbonyl Compounds
作者:Wei Zhang、Gabriel M. Johnson、Zhi Guan、Yan-Hong He
DOI:10.1002/adsc.201801032
日期:2018.12.3
sulfinic acids to access both E‐ and Z‐β‐sulfonyl‐α,β‐unsaturated carbonyl compounds has been developed. We propose that this reaction via a hydroxylallene intermediate delivers the thermodynamically stable E isomer, or via a concerted termolecular AdE3 mechanism affords Z isomer. The stereoselectivity of addition (syn or anti) can be controlled by varying the sulfonyl sources and acidic buffer solutions
已经开发出一种电子不足的炔烃,通过亚磺酸钠或亚磺酸进行无金属的氢磺酰化反应,以同时获得E-和Z - β-磺酰基-α,β-不饱和羰基化合物。我们建议该反应通过羟基丙二烯中间体传递热力学稳定的E异构体,或通过一致的分子Ad E 3机理提供Z异构体。加成的立体选择性(合成或反合成)可以通过改变磺酰基来源和酸性缓冲溶液来控制。该协议展示了内部或末端炔烃的广泛底物范围,包括各种取代的炔酮和炔基酯。这种方法温和,高效,操作简单且易于扩展。