In 2020 ANGEW CHEM INT EDIT published article about DYNAMIC KINETIC RESOLUTION; CHALCOGEN-CHALCOGEN INTERACTIONS; ENANTIOSELECTIVE SYNTHESIS; PIVALIC ANHYDRIDE; ATROPOSELECTIVE SYNTHESIS; NONCOVALENT INTERACTIONS; DENSITY FUNCTIONALS; DIPHENYLACETIC ACID; CHIRAL BIARYLS; ALCOHOLS in [Munday, Elizabeth S.; Young, Claire M.; Slawin, Alexandra M. Z.; Smith, Andrew D.] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland; [Grove, Markas A.; Feoktistova, Taisiia; Brueckner, Alexander C.; Walden, Daniel M.; Cheong, Paul Ha-Yeon] Oregon State Univ, Dept Chem, 153 Gilbert Hall, Corvallis, OR 97331 USA; [Campbell, Andrew D.] AstraZeneca, Pharmaceut Technol & Dev, Silk Rd Business Pk, Macclesfield SK10 2NA, Cheshire, England in 2020, Cited 94. The Name is Benzoic anhydride. Through research, I have a further understanding and discovery of 93-97-0. Formula: C14H10O3
Axially chiral phenols are attractive targets in organic synthesis. This motif is central to many natural products and widely used as precursors to, or directly, as chiral ligands and catalysts. Despite their utility few simple catalytic methods are available for their synthesis in high enantiopurity. Herein the atropselective acylation of a range of symmetric biaryl diols is investigated using isothiourea catalysis. Studies on a model biaryl diol substrate shows that the high product er observed in the process is a result of two successive enantioselective reactions consisting of an initial enantioselective desymmetrization coupled with a second chiroablative kinetic resolution. Extension of this process to a range of substrates, including a challenging tetraorthosubstituted biaryl diol, led to highly enantioenriched products (14 examples, up to 98:2 er), with either HyperB(TM) or B-TM identified as the optimal catalyst depending upon the substitution pattern within the substrate. Computation has been used to understand the factors that lead to high enantiocontrol in this process, with maintenance of planarity to maximize a 1,5-S…O interaction within the key acyl ammonium intermediate identified as the major feature that determines atropselective acylation and thus product enantioselectivity.
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Reference:
Isothiazole – Wikipedia,
,Isothiazole – ScienceDirect.com