Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides. Issue 29 (20th July 2017)

• Record Type: Journal Article
• Authors: Kroc, Michelle A.; Patil, Aditi; Carlos, Anthony; Ballantine, Josiah; Aguilar, Stephanie; Mo, Dong-Liang; Wang, Heng-Yen; Mueller, Daniel S.; Wink, Donald J.; Anderson, Laura L.
• Is Part Of: Tetrahedron. Volume 73:Issue 29(2017)
• Page Start: 4125
• Page End: 4137
• Publication Date: 2017-07-20
• Subjects: α-Oxygenation -- Catechol -- [3, 3]-Rearrangement -- Chan-Lam -- Boronic acid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.01.061
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A common approach to the synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3, 3]-rearrangements of N -enoxyphthalimides, N -enoxyisoindolinones, and N -aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations facilitate the dioxygenation of alkenylboronic acids for the synthesis of α-oxygenated ketones and the dioxygenation of arylboronic acids for the synthesis of catechols. The rearrangements of N -enoxyisoindolinones have also been shown to be diastereoselective. Graphical abstract: