The preparation of C-arylglycals has been accomplished employing the Suzuki-Miyaura cross-coupling reaction of dihydropyranylphosphates with arylboronate esters. The reaction is tolerant of both electron-donating (EDG) and electron-withdrawing (EWG) groups on the aromatic ring and affords the corresponding C-arylglycals in good to excellent yields (68-97%). Additionally, the ketene acetal phosphate derived from 6-deoxy-3,4-di-O-benzyl-L-rhamnal also couples efficiently to yield C-arylglycals in excellent yields.
Preparation of C-Arylglycals via Suzuki-Miyaura Cross-Coupling of Dihydropyranylphosphates. -The Suzuki-Miyaura cross-coupling of dihydropyranylphosphates with various arylboronate esters affords the corresponding arylated dihydropyrans including C-arylated glycal (V). -(LEIDY, M. R.; HOFFMAN, M. J.; PONGDEE*, R.; Tetrahedron Lett. 54 (2013) 50, 6889-6891, http://dx.
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