期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 -, 期 -, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202300419
关键词
Asymmetric Synthesis; Atropisomers; Chiral Phosphoric Acid; N,N '-Bisindoles; Organocatalysis
This study introduces a novel strategy for the enantioselective synthesis of axially chiral N,N'-bisindoles using chiral phosphoric acid-catalyzed formal cycloadditions. The synthesized compounds showed excellent yields and enantioselectivities, and exhibited cytotoxicity towards cancer cells. Moreover, they were also transformed into axially chiral phosphine ligands with high catalytic activity.
This study establishes the first organocatalytic enantioselective synthesis of axially chiral N,N '-bisindoles via chiral phosphoric acid-catalyzed formal (3+2) cycloadditions of indole-based enaminones as novel platform molecules with 2,3-diketoesters, where de novo indole-ring formation is involved. Using this new strategy, various axially chiral N,N '-bisindoles were synthesized in good yields and with excellent enantioselectivities (up to 87 % yield and 96 % ee). More importantly, this class of axially chiral N,N '-bisindoles exhibited some degree of cytotoxicity toward cancer cells and was derived into axially chiral phosphine ligands with high catalytic activity. This study provides a new strategy for enantioselective synthesis of axially chiral N,N '-bisindoles using asymmetric organocatalysis and is the first to realize the applications of such scaffolds in medicinal chemistry and asymmetric catalysis.
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