期刊
TETRAHEDRON
卷 73, 期 29, 页码 4125-4137出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.01.061
关键词
alpha-Oxygenation; Catechol; [3,3]-Rearrangement; Chan-Lam; Boronic acid
资金
- National Science Foundation [NSF-CHE 1212895, 1464115]
- ACS PRF [DNI 50491]
- University of Illinois at Chicago
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1464115] Funding Source: National Science Foundation
A common approach to the synthesis of alpha-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 alpha-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. (C) 2017 Elsevier Ltd. All rights reserved.
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