1402704-26-0Relevant articles and documents
Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides
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.
, p. 4125 - 4137 (2017/06/29)
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.
Preparation of α-oxygenated ketones by the dioxygenation of alkenyl boronic acids
Patil, Aditi S.,Mo, Dong-Liang,Wang, Heng-Yen,Mueller, Daniel S.,Anderson, Laura L.
, p. 7799 - 7803 (2012/09/08)
Two in two: Dioxygenation of alkenyl boronic acids has been achieved with N-hydroxyphthalimide. The two-step process involves etherification of an alkenyl boronic acid with N-hydroxyphthalimide followed by a [3,3] rearrangement. The dioxygenated product can then be hydrolyzed to form either the corresponding α-hydroxy ketone or the α-benzoyloxy ketone. Copyright