Stereochemical modulation of ketyl radical cyclization enabled by pyridine-boryl radicals: catalytic diastereoselective synthesis of trans-2-alkyl-1-indanols DOI

Somi Kim,

Junhyuk Jo,

Sunggi Lee

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(80), С. 11983 - 11986

Опубликована: Янв. 1, 2023

Previously available ketyl radical cyclization conditions suffer from low and uncontrollable diastereoselectivity because of the absence reagent-substrate interactions. In this report, stereochemical modulation was accomplished by taking advantage pyridine-boryl radical, which leaves synthetically modifiable boronate moiety on carbonyl oxygen near reacting center during stereo-determining step. consequence, a catalytic diastereoselective synthesis trans-2-substituted-1-indanols achieved in presence sterically congested six-membered diboronic ester an efficient hydrogen atom donor.

Язык: Английский

TBAB-catalyzed assisted C-C/C-N bond formations: An efficient approach to dihydrobenzo[ b ][1,8]naphthyridin derivatives via metal free Cascade annulation DOI
Jiming Liu, Xinghua Zheng, Wenjun Luo

и другие.

Synthetic Communications, Год журнала: 2024, Номер 54(15), С. 1252 - 1262

Опубликована: Июль 22, 2024

Язык: Английский

Процитировано

1

Recent Advances in the Development of Indolizine Scaffolds: Synthetic Methodology and Mechanistic Insights DOI
Jiuzhong Huang, Chunsheng Li, Xiaoning Li

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 20, 2024

Comprehensive Summary Indolizine is a nitrogen‐containing heterocycle with strong aromaticity, possessing delocalized 10π‐electron system. Based on the indolizine scaffolds, numerous molecules biological activity and organic functional materials have been synthesized. Since 2016, over 110 papers published synthesis of but reviews synthesizing scaffolds incomplete not up‐to‐date. Herein, from perspective structure combination pyrrole pyridine ring, we focus construction through diversity starting substrates, including derivatives (N1‐substituted pyridinium salt derivatives, C2‐substituted N1‐ C2‐free substituted derivatives), unoriginal ring substrates. Furthermore, corresponding reaction mechanisms synthetic methodologies are also elaborated. Therefore, this review only paves way for provides insight into exploring new modes constructing heterocycles. Key Scientists was discovered by Angeli in 1890 first prepared Scholtz 1912 α‐picoline acetic anhydride. A general approach developed Chichibabin 1927, that practical value preparation 2‐alkyl‐ or 2‐arylindolizines. The closure quaternary halides. At begining 21st century, Basavaiah introduced dimension Baylis‐Hillman chemistry leading to novel facile convenient methodology one‐pot operation. In 2010, Barluenga reported Cu(I)‐catalyzed regioselective [3+2] cyclization unsubstituted pyridines toward alkenyldiazoacetates functionalized successful example metal‐catalyzed π‐deficient heterocyclic system alkenyldiazo compounds. 2019 2022, Xi Liu exploited methods non‐pyridine as synthesize indolizines, respectively. Guo an environmentally benign electrooxidative formyl‐ acyl‐substituted indolizines.

Язык: Английский

Процитировано

1

Mn(OAc)2-promoted [3+2] cyclization of enaminone with isocyanoacetate: Rapid access to pyrrole-2-carboxylic ester derivatives with potent anticancer activity DOI
Jiuzhong Huang, Yi Wu, Zhihao Hu

и другие.

Bioorganic Chemistry, Год журнала: 2023, Номер 140, С. 106748 - 106748

Опубликована: Июль 28, 2023

Язык: Английский

Процитировано

3

Access to thiionized-, selenolized-, and alkylated 5-alkylidene 3-pyrrolin-2-one derivatives via a regioselective oxidative annulation reaction DOI
Donghan Liu, Siyu Song,

Longkun Chen

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(12), С. 2596 - 2602

Опубликована: Янв. 1, 2023

A metal-free regioselective oxidative annulation reaction of readily available 2,4-pentanediones with primary amines has been described. This protocol provides a divergent strategy for the incorporation various radical donors into 5-alkylidene 3-pyrrolin-2-one skeletons, producing variety thiionized-, selenolized-, and alkylated derivatives. Moreover, diverse synthetic transformations products were also investigated.

Язык: Английский

Процитировано

2

Stereochemical modulation of ketyl radical cyclization enabled by pyridine-boryl radicals: catalytic diastereoselective synthesis of trans-2-alkyl-1-indanols DOI

Somi Kim,

Junhyuk Jo,

Sunggi Lee

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(80), С. 11983 - 11986

Опубликована: Янв. 1, 2023

Previously available ketyl radical cyclization conditions suffer from low and uncontrollable diastereoselectivity because of the absence reagent-substrate interactions. In this report, stereochemical modulation was accomplished by taking advantage pyridine-boryl radical, which leaves synthetically modifiable boronate moiety on carbonyl oxygen near reacting center during stereo-determining step. consequence, a catalytic diastereoselective synthesis trans-2-substituted-1-indanols achieved in presence sterically congested six-membered diboronic ester an efficient hydrogen atom donor.

Язык: Английский

Процитировано

2