Chiral Phosphoric Acid-Catalyzed Enantioselective Pictet–Spengler Reaction for Concise Synthesis of CF3-Substituted Tetrahydro-β-Carbolines DOI Creative Commons
Shigenobu Umemiya, Susheel J. Nara, Masahiro Terada

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Июнь 3, 2025

Fluorine-containing compounds are widely found in pharmaceuticals, agrochemicals, and functional materials. In particular, containing enantioenriched trifluoromethyl groups essential because they show metabolic stability, lipophilicity, membrane permeability vivo. this study, an enantioselective Pictet-Spengler reaction of tryptamine derivatives with 1,1,1-trifluoro-4-[tris(1-methylethyl)silyl]-3-butyn-2-one catalyzed by a chiral phosphoric acid is demonstrated, which provides CF3-containing tetrahydro-β-carboline good yields high enantioselectivities.

Язык: Английский

Recent advancements in visible-light-induced direct C(3)–H functionalization of quinoxalin-2(1H)-ones DOI Creative Commons

Xin Han,

Yifan Guo, Y. Hu

и другие.

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Дек. 1, 2024

Язык: Английский

Процитировано

3
Biocatalytic Reduction of Double Carbon-Nitrogen Bonds Toward Chiral Amines DOI

J. González-Rodríguez,

Florian Rudroff

Elsevier eBooks, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0
Enantioselective Synthesis of Chiral Fluorinated Amines via Manganese-Catalyzed Asymmetric Hydrogenation DOI

Xin‐Hu Hu,

Kaikai Zheng,

Hang Yin

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 28, 2025

A highly enantioselective Mn-catalyzed hydrogenation of fluorinated imines has been realized. The success this is attributed to the use chiral ferrocenyl P,N,N ligand bearing an additional center at pyridinylmethyl position. displayed broad functional group tolerance, thus furnishing a wide range optically active amines with up 98% enantiomeric excess. utility methodology well-demonstrated by scale-up asymmetric N-(4′-methoxyphenyl)-ethan-2,2,2-trifluoro-1-phenyl-1-imine.

Язык: Английский

Процитировано

0
Visible-Light-Driven Tandem Cyclization of o-Hydroxyaryl Enaminones: Access to 3-(α-Arylsulfonamido)trifluoroethyl Chromones DOI
Jinwei Yuan, Qiang Liu,

X. H. Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 22, 2025

A visible-light-driven intermolecular tandem α-amidotrifluoroethylation/cyclization of enaminones using a previously unreported N-trifluoroethylaminopyridinium salt was achieved in the absence transition metal catalysts or bases. Notable features this synthetic method include mild conditions, high selectivity, excellent functional group compatibility, and satisfactory yields. Preliminary mechanistic studies indicate that reaction proceeds via radical pathway, involving an situ generated N-trifluoroethyl radical, followed by 1,2-H shift.

Язык: Английский

Процитировано

0
Chiral Phosphoric Acid-Catalyzed Enantioselective Pictet–Spengler Reaction for Concise Synthesis of CF3-Substituted Tetrahydro-β-Carbolines DOI Creative Commons
Shigenobu Umemiya, Susheel J. Nara, Masahiro Terada

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Июнь 3, 2025

Fluorine-containing compounds are widely found in pharmaceuticals, agrochemicals, and functional materials. In particular, containing enantioenriched trifluoromethyl groups essential because they show metabolic stability, lipophilicity, membrane permeability vivo. this study, an enantioselective Pictet-Spengler reaction of tryptamine derivatives with 1,1,1-trifluoro-4-[tris(1-methylethyl)silyl]-3-butyn-2-one catalyzed by a chiral phosphoric acid is demonstrated, which provides CF3-containing tetrahydro-β-carboline good yields high enantioselectivities.

Язык: Английский

Процитировано

0