3951-10-8Relevant articles and documents
Regioselective C2- and C8-acylation of 5,11-dihydroindolo[3,2-b]carbazoles and the synthesis of their 2,8-bis(quinoxalinyl) derivatives
Irgashev, Roman A.,Kazin, Nikita A.,Kim, Grigory A.,Rusinov, Gennady L.,Charushin, Valery N.
, p. 3561 - 3572 (2015)
An efficient approach for the double acetylation of 5,11-dihexyl-6,12-di(hetero)aryl-substituted 5,11-dihydroindolo[3,2-b]carbazoles with acetic anhydride in the presence of boron trifluoride etherate has been developed, thus affording the corresponding 2
Enantioselective Synthesis of 3,5,6-Substituted Dihydropyranones and Dihydropyridinones using Isothiourea-Mediated Catalysis
Stark, Daniel G.,Morrill, Louis C.,Cordes, David B.,Slawin, Alexandra M. Z.,O'Riordan, Timothy J. C.,Smith, Andrew D.
supporting information, p. 395 - 400 (2016/05/19)
The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea-catalyzed processes has been expanded and explored through the use of 2-N-tosyliminoacrylates and 2-aroylacrylates in a Michael addition-lactonization/lactamization cascade reaction. Notably, to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2-aroyl acrylates, while carboxylic acids can be used with 2-N-tosyliminoacrylates, delivering a range of 3,5,6-substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90 % ee). The derivatization of the heterocyclic core of a 3,5,6-substituted dihydropyranone through hydrogenation is also reported.
Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines
Smith, Siobhan R.,Fallan, Charlene,Taylor, James E.,McLennan, Ross,Daniels, David S. B.,Morrill, Louis C.,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information, p. 10530 - 10536 (2015/07/07)
A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high d.r., yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.