Strategies for the synthesis of 2-substituted indoles and indolines starting from acyclic alpha-phosphoryloxy enecarbamates.
Strategies have been developed for the synthesis of 2-substituted indoles and indolines starting from acyclic alpha-phosphoryloxy enecarbamates. A highly chemoselective cross-coupling of N-(o-bromophenyl)-alpha-phosphoryloxyenecarbamates with boron nucleophiles enabled the efficient preparation of various N-(o-bromophenyl)enecarbamates, which served as useful precursors for subsequent Heck-type cyclization or 5-endo-trig aryl radical cyclization to furnish 2-substituted indoles or indolines, respectively.
Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-amamiya, Sendai 981-8555, Japan. hfuwa@bio.tohoku.ac.jp
Haruhiko
H
Fuwa
Makoto
M
Sasaki
D001896:Boron Compounds; D002219:Carbamates / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis*
D001896:Boron Compounds; D002219:Carbamates; D007211:Indoles; C057812:indoline