Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 15, Pages 10427-10439Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01105
Keywords
-
Categories
Funding
- National Natural Science Foundation of China [21772069, 21831007]
- Six Kinds of Talents Project of Jiangsu Province [SWYY-025]
Ask authors/readers for more resources
The study focuses on the catalytic asymmetric dearomative cycloaddition of 3-alkyl-2-vinylindoles using chiral phosphoric acid, resulting in the synthesis of chiral pyrroloindolines with two tetrasubstituted stereogenic centers in good yields and excellent stereoselectivities. This reaction introduces new reactivity to 3-alkyl-2-vinylindoles and presents a potential strategy for discovering anti-cancer drug candidates.
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available