Version 2 2021-07-27, 19:09Version 2 2021-07-27, 19:09
Version 1 2021-07-27, 12:39Version 1 2021-07-27, 12:39
journal contribution
posted on 2021-07-27, 19:09authored byKe-Wei Chen, Dan-Dan Wang, Si-Jia Liu, Xue Wang, Yu-Chen Zhang, Yi-Ming Tian, Qiong Wu, Feng Shi
The first application of 3-alkyl-2-vinylindoles
in catalytic asymmetric
dearomative cycloadditions was established by chiral phosphoric acid
(CPA)-catalyzed (2+3) cycloaddition with azoalkenes, leading to the
generation of chiral pyrroloindolines bearing two tetrasubstituted
stereogenic centers in good yields (61–96%) and excellent stereoselectivities
(all >95:5 dr, 86–99% ee). This reaction has realized the
first
enantioselective dearomative cycloaddition of 3-alkyl-2-vinylindoles,
which brings a new reactivity to this class of vinylindoles and will
enrich the chemistry of 3-alkyl-2-vinylindoles. In addition, this
approach has provided a useful strategy for the construction of enantioenriched
pyrroloindoline skeletons bearing two tetrasubstituted stereogenic
centers. More importantly, the bioassay of these chiral pyrroloindolines
has revealed that some compounds exhibit strong anti-cancer activity
against Hela and MCF-7 cell lines, which will be helpful for discovering
anti-cancer drug candidates.