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- W4280600344 abstract "Abstract Hydroxylative dearomatization reactions of phenols (HPD) offer an efficient way to assemble complex, biologically 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, we describe a highly enantioselective, organocatalytic tandem o‐HPD‐[4+2] reaction. Our methodology 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 our conditions was demonstrated at gram‐scale, using an amine precatalyst, accessible in a single synthetic step." @default.
- W4280600344 created "2022-05-22" @default.
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- W4280600344 date "2022-06-10" @default.
- W4280600344 modified "2023-10-11" @default.
- W4280600344 title "Organocatalytic Enantioselective Synthesis of Bicyclo[2.2.2]octenones via Oxaziridinium Catalysed <i>ortho</i>‐Hydroxylative Phenol Dearomatization**" @default.
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- W4280600344 doi "https://doi.org/10.1002/anie.202205278" @default.
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