Light-driven redox deracemization of indolines and tetrahydroquinolines using a photocatalyst coupled with chiral phosphoric acid.

Qipeng Chen, Yuanli Zhu, Xujing Shi, Renfu Huang, Chuang Jiang, Kun Zhang, Guohua Liu

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Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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7 authors at 1 institution in 1 country.

Qipeng ChenInternational Joint Laboratory on Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University Shanghai 200234 P. R. China ghliu@shnu.edu.cn zhangkun@shnu.edu.cn.

Yuanli ZhuInternational Joint Laboratory on Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University Shanghai 200234 P. R. China ghliu@shnu.edu.cn zhangkun@shnu.edu.cn.

Xujing ShiInternational Joint Laboratory on Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University Shanghai 200234 P. R. China ghliu@shnu.edu.cn zhangkun@shnu.edu.cn.

Renfu HuangInternational Joint Laboratory on Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University Shanghai 200234 P. R. China ghliu@shnu.edu.cn zhangkun@shnu.edu.cn.

Chuang JiangInternational Joint Laboratory on Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University Shanghai 200234 P. R. China ghliu@shnu.edu.cn zhangkun@shnu.edu.cn.

Kun ZhangInternational Joint Laboratory on Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University Shanghai 200234 P. R. China ghliu@shnu.edu.cn zhangkun@shnu.edu.cn.

Guohua LiuInternational Joint Laboratory on Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University Shanghai 200234 P. R. China ghliu@shnu.edu.cn zhangkun@shnu.edu.cn.ORCID https://orcid.org/0000-0001-8407-3095

Shanghai Normal University · CN

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The integration of oxidation and enantioselective reduction enables a redox deracemization to directly access enantioenriched products from their corresponding racemates. However, the solution of the kinetically microscopic reversibility of substrates used in this oxidation/reduction unidirectional event is a great challenge. To address this issue, we have developed a light-driven strategy to enable an efficient redox deracemization of cyclamines. The method combines a photocatalyst and a chiral phosphoric acid in a toluene/aqueous cyclodextrin emulsion biphasic co-solvent system to drive the cascade out-of-equilibrium. Systemic optimizations achieve a feasible oxidation/reduction cascade sequence, and mechanistic investigations demonstrate a unidirectional process. This single-operation cascade route, which involves initial photocatalyzed oxidation of achiral cyclamines to cyclimines and subsequent chiral phosphoric acid-catalyzed enantioselective reduction of cyclimines to chiral cyclamines, is suitable for constructing optically pure indolines and tetrahydroquinolines.

Identifiers

PMID36819858

DOI10.1039/d2sc06340a

PMCPMC9930931

OpenAlexW4313886413

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LicenceCC BY

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.