Formation of trisubstituted buta-1,3-dienes and α,β-unsaturated ketones via the reaction of functionalized vinyl phosphates and vinyl phosphordiamidates with organometallic reagents†,10.1039/D0RA07472A

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Formation of trisubstituted buta-1,3-dienes and α,β-unsaturated ketones via the reaction of functionalized vinyl phosphates and vinyl phosphordiamidates with organometallic reagents†

Petr Oeser,Jakub Koudelka,Hana Dvořáková,Tomáš Tobrman

RSC Advances Pub Date : 09/22/2020 00:00:00 , DOI:10.1039/D0RA07472A

Abstract

We studied the reactions of vinyl phosphates and vinyl phosphordiamidates containing an ester functional group with organometallic reagents. We found that the functionalized vinyl phosphates were smoothly converted into tri- and tetrasubstituted buta-1,3-dienes via the reaction with aryllithium reagents. Moreover, the vinyl phosphordiamidates were converted into α,β-unsaturated ketones using Grignard reagents. Based on the performed experiments, we proposed a reaction mechanism, which was confirmed by means of the isolation of key intermediates.