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The development of enantioselective pinacol rearrangement is ex-tremely challenging due to the likelihood involvement of the carbeni-um intermediate that renders the stereochemical communication between catalyst and substrate difficult to achieve.… Click to show full abstract
The development of enantioselective pinacol rearrangement is ex-tremely challenging due to the likelihood involvement of the carbeni-um intermediate that renders the stereochemical communication between catalyst and substrate difficult to achieve. Herein, we report chiral N-triflyl phosphoramide-catalyzed enantioselective pinacol rearrangement of 1,2-tertiary diols and mechanistically related Meinwald rearrangement of tetrasubstituted epoxides for the synthe-sis of enantioenriched 2-alkynyl-2-arylcyclohexanones and 2,2-diarylcyclohexanones, respectively. Total synthesis of (+)-mesembrane featuring the catalytic enantioselective pinacol rear-rangement as a key strategic step is also documented.
Journal Title: Journal of the American Chemical Society
Year Published: 2019
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