Synthesis of Axially Chiral N‐Arylindoles via Atroposelective Cyclization of Ynamides Catalyzed by Chiral Brønsted Acids

In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble‐metal catalysis. Herein, a facile access to axially chira...

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Published inAngewandte Chemie International Edition Vol. 61; no. 20; pp. e202201436 - n/a
Main Authors Wang, Ze‐Shu, Zhu, Lu‐Jing, Li, Cui‐Ting, Liu, Bin‐Yang, Hong, Xin, Ye, Long‐Wu
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 09.05.2022
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkynes
Asymmetry
Axial Chirality
Brønsted Acids
Catalysis
Chemistry
Chemistry, Multidisciplinary
Chirality
Heterocycles
Organocatalysis
Physical Sciences
Science & Technology
Heterocycles
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
REACTIVITY
SULFONAMIDES
DEPROTECTION
Organocatalysis
INDOLES
Bronsted Acids
Axial Chirality
CONSTRUCTION
C-C
ACCESS
Alkynes
Brønsted Acids
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Summary:In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble‐metal catalysis. Herein, a facile access to axially chiral N‐heterocycles enabled by chiral Brønsted acid‐catalyzed 5‐endo‐dig cyclization of ynamides is disclosed, which represents the first metal‐free protocol for the construction of axially chiral compounds from ynamides. This method allows the practical and atom‐economical synthesis of valuable N‐arylindoles in excellent yields with generally excellent enantioselectivities. Moreover, organocatalysts and ligands based on such axially chiral N‐arylindole skeletons are demonstrated to be applicable to asymmetric catalysis. A chiral Brønsted acid‐catalyzed atroposelective cyclization of ynamides is disclosed, which represents the first metal‐free protocol for the construction of axially chiral compounds from ynamides. This method enables the practical and atom‐economical synthesis of valuable N‐arylindoles in excellent yields with generally excellent enantioselectivities.
Bibliography:These authors contributed equally to this work.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202201436