1176861-76-9Relevant academic research and scientific papers
Isothiourea-catalyzed enantioselective α-alkylation of esters via 1,6-conjugate addition to para-quinone methides
Arokianathar, Jude N.,Greenhalgh, Mark D.,Hartley, Will C.,McLaughlin, Calum,Ng, Sean,Slawin, Alexandra M. Z.,Smith, Andrew D.,Stead, Darren
supporting information, (2021/11/01)
The isothiourea-catalyzed enantioselective 1,6-conjugate addition of para-nitrophenyl esters to 2,6-disubstituted para-quinone methides is reported. para-Nitrophenoxide, generated in situ from initial N-acylation of the isothiourea by the para-nitrophenyl ester, is proposed to facilitate catalyst turnover in this transformation. A range of para-nitrophenyl ester products can be isolated, or derivatized in situ by addition of benzylamine to give amides at up to 99% yield. Although low diastereocontrol is observed, the diastereoisomeric ester products are separable and formed with high enantiocontrol (up to 94:6 er).
Copper-Catalyzed 1,6-Hydrodifluoroacetylation of para-Quinone Methides at Ambient Temperature with Bis(pinacolato)diboron as Reductant
Ke, Miaolin,Song, Qiuling
supporting information, p. 384 - 389 (2017/02/10)
An original and efficient copper-catalyzed 1,6-hydrodifluoroacetylation of para-quinone methides with difluoroalkyl bromides has been described with bis(pinacolato)diboron (B2pin2) as reductant. In this reaction, a new C(sp3)–CF2bond is constructed under smart conditions. A broad substrate scope of para-quinone methides (p-QMs) make this protocol very practical and attractive. Preliminary mechanistic studies manifested that a difluoroalkyl radical pathway was involved in this reaction. Also the presence of the diboron reagent was an essential requisite in this transformation. (Figure presented.).
Synthesis and characterization of novel quinone methides: Reference electrophiles for the construction of nucleophilicity scales
Richter, Dorothea,Hampel, Nathalie,Singer, Thomas,Ofial, Armin R.,Mayr, Herbert
experimental part, p. 3203 - 3211 (2009/12/09)
Novel synthetic routes to the aryl-substituted quinone methides 3a-f have been developed, and a previously reported Mannich approach has been used for the syntheses of the acceptor substituted quinone methides 2e-g. The secondorder rate constants for the
