D′Arcy, Tom D. published the artcileOrganocatalytic Enantioselective Synthesis of Bicyclo[2.2.2]octenones via Oxaziridinium Catalysed ortho-Hydroxylative Phenol Dearomatization, HPLC of Formula: 126613-06-7, the publication is Angewandte Chemie, International Edition (2022), 61(30), e202205278, database is CAplus and MEDLINE.
Hydroxylative dearomatization reactions of phenols (HPD) offer an efficient way to assemble complex, biol. relevant scaffolds. Despite this, enantioselective hydroxylative phenol dearomatizations for the construction of bicyclo[2.2.2]octenones are classically limited to stoichiometric chiral reagents, and a practical, enantioselective catalytic method has remained elusive. Herein, authors describe a highly enantioselective, organocatalytic tandem o-HPD-[4+2] reaction. Authors methodol. utilizes a chiral oxaziridinium organocatalyst, that is available in both enantiomeric forms, to afford dearomatized products in high enantioselectivity over a range of phenol substitution patterns. This approach was applied to the highly enantioselective synthesis of (+)-biscarvacrol (99 : 1 e.r.) and (-)-bis(2,6-xylenol) (94 : 6 e.r.). The practicality of authors conditions was demonstrated at gram-scale, using an amine precatalyst, accessible in a single synthetic step.
Angewandte Chemie, International Edition published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, HPLC of Formula: 126613-06-7.
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