Isothiourea catalysed enantioselective generation of point and axially chiral iminothia- and iminoselenazinanones.

ABSTRACT: Symmetrical and unsymmetrical thioureas, as well as unsymmetrical selenoureas, are used in an isothiourea-catalysed Michael addition-lactamisation protocol using α,β-unsaturated pentafluorophenyl esters to generate iminothia- and iminoselenazinanone heterocycles with high enantioselectivity (up to 99 : 1 er). The scope and limitations of this process have been widely investigated (40 examples in total) with unsymmetrical thio- and selenoureas containing ortho-substituted N-aryl substituents giving atropisomeric products, leading to an effective process for iminothia- and iminoselenazinanones heterocyclic products containing both point and axially chiral stereogenic elements with excellent stereocontrol (up to >95 : 5 dr and 98 : 2 er). Mechanistic investigation showed that (i

SUBMITTER: Nimmo AJ 

PROVIDER: S-EPMC12068085 | biostudies-literature | 2025 Jun

REPOSITORIES: biostudies-literature