Enantioselective Synthesis of 2-Aryl-3,3-Disubstituted Indolines from 3<i>H</i>-Indoles via Deracemization

An enantioselective synthesis of 2-aryl 3,3-disubstituted 3<i>H</i>-indoles has been successfully developed via a deracemization process involving borane-catalyzed hydrogenation and chiral phosphoric-acid-catalyzed asymmetric transfer hydrogenation. A variety of 3<i>H</i>-indoles were effective substrates to afford the desired indolines in 86-95% yields with 45-92% ee's.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-08
DOI
https://doi.org/10.1021/acs.joc.5c00100
Citations
2
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
1.87

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article

Enantioselective Synthesis of 2-Aryl-3,3-Disubstituted Indolines from 3H-Indoles via Deracemization

Guangyu Cui, Zaiqi Han, Xiangqing Feng, Haifeng Du
2 citations
The Journal of Organic Chemistry
Organoboron and organosilicon chemistry
1.87
article

Enantioselective Synthesis of 2-Aryl-3,3-Disubstituted Indolines from 3H-Indoles via Deracemization

Guangyu Cui, Zaiqi Han, Xiangqing Feng, Haifeng Du
article en
2 citations

Abstract

An enantioselective synthesis of 2-aryl 3,3-disubstituted 3<i>H</i>-indoles has been successfully developed via a deracemization process involving borane-catalyzed hydrogenation and chiral phosphoric-acid-catalyzed asymmetric transfer hydrogenation. A variety of 3<i>H</i>-indoles were effective substrates to afford the desired indolines in 86-95% yields with 45-92% ee's.

The Journal of Organic ChemistryVol. 90(15)
Chinese Academy of Sciences (CN), Beijing National Laboratory for Molecular Sciences (CN), University of Chinese Academy of Sciences (CN)
National Natural Science Foundation of China, National Key Research and Development Program of China
Zero hunger
Openalex Percentile: Top 17%
Organoboron and organosilicon chemistry
1.87
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