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- W4206387271 abstract "Abstract α‐aryl α,β‐unsaturated carbonyls represent an important class of derivatizable synthetic intermediates, however, the synthesis of such compounds still remains a challenge. Recently, we showcased a novel Z ‐selective α‐arylation of α,β‐unsaturated nitriles with aryl sulfoxides via [3,3]‐rearrangement involving an Morita–Baylis–Hillman (MBH) process. Herein, we demonstrate the feasibility of reversing the stereoselectivity of such MBH‐type [3,3]‐rearrangement by switching to a new pair of rearrangement partners consisting of aryl iodanes and α,β‐unsaturated oxazolines. As a result, the two protocols complement each other in approaching E ‐ or Z ‐α‐aryl α,β‐unsaturated carbonyl derivatives. Mechanistic studies reveal a possible reaction pathway and provide an explanation for the opposite stereoselectivities." @default.
- W4206387271 created "2022-01-26" @default.
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- W4206387271 date "2021-04-07" @default.
- W4206387271 modified "2023-10-16" @default.
- W4206387271 title "Morita–Baylis–Hillman‐Type [3,3]‐Rearrangement: Switching from <i>Z</i> ‐ to <i>E</i> ‐Selective α‐Arylation by New Rearrangement Partners" @default.
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- W4206387271 doi "https://doi.org/10.1002/ange.202100497" @default.
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