Enantioenriched BoronC,N‐Chelates via Chirality Transfer DOI Creative Commons
Yannick Stöckl,

Ethan J. Tait,

Wolfgang Frey

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(41)

Опубликована: Май 5, 2023

Molecules stereogenic only at tetrahedral boron atoms show great promise for applications, example as chiroptical materials, but are scarcely investigated due to their synthetic challenge. Hence, this study reports a two-step synthesis of enantioenriched C,N-chelates. First, the diastereoselective complexation alkyl/aryl borinates with chiral aminoalcohols furnished heterocycles in up 86 % yield and d.r. >98 : 2. Treatment these O,N-complexes chelate nucleophiles was surmised transfer stereoinformation via ate-complex into C,N-products. This chirality succeeded by substitution O,N-chelates lithiated phenyl pyridine give C,N-chelates 84 e.r. 97 3. The aminoalcohol ligands could be recovered after isolation tolerated alkyl, alkynyl (hetero-)aryl moieties further extended post-modification: transformations such catalytic hydrogenations or sequential deprotonation/electrophilic trapping were feasible while maintaining stereochemical integrity Structural aspects chelates studied variable temperature NMR X-ray diffraction.

Язык: Английский

Stereospecific alkenylidene homologation of organoboronates by SNV reaction DOI
Miao Chen,

Christian D. Knox,

Mithun C. Madhusudhanan

и другие.

Nature, Год журнала: 2024, Номер 631(8020), С. 328 - 334

Опубликована: Май 23, 2024

Язык: Английский

Процитировано

6
Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes DOI Creative Commons

Yu-Wen Sun,

Jingkun Zhao,

Xinyu Yan

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Дек. 30, 2024

The strain-release-driven reactions of bicyclo[1.1.0]butanes (BCBs) have received significant attention from chemists. Notably, 1,2-migratory enabled by BCB-derived B-ate complexes effectively complement the initiated common BCBs. desired products are particularly valuable for late-stage transformations due to presence C-B bond. However, asymmetric mediated boronate progressed slowly. In this study, we develop an synthesis atropisomers featuring cis-cyclobutane boronic esters facilitated 1,2-carbon or boron migration ring-strained complexes, achieving high enantioselectivity. reaction is compatible with various aryl, alkenyl, alkyl and B

Язык: Английский

Процитировано

4
Diversifying fluoroalkanes: light-driven fluoroalkyl transfer via vinylboronate esters DOI Creative Commons
Kaushik Chakrabarti,

Chandana Sunil,

Benjamin M. Farris

и другие.

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A metal-free strategy to access tertiary difluoromethylene-containing molecules from RCF 2 H (R = aryl, H, F) precursors, vinyl-pinacol boronic ester (BPin) reagents, and proradical reagents is reported.

Язык: Английский

Процитировано

0
Strategic 1,n-migration of boronate complexes: a novel platform for remote C–C bond construction DOI
Yiming Chen, Xue Li, Zhigang Xu

и другие.

Molecular Diversity, Год журнала: 2025, Номер unknown

Опубликована: Апрель 2, 2025

Язык: Английский

Процитировано

0
Nickel-catalyzed C(sp2)−C(sp3) cross-coupling to access benzyl Bpins of arylboronic acids with α-halo boronic esters DOI Creative Commons

Yang Sun,

Chongwei Zhu, Hui Wang

и другие.

Communications Chemistry, Год журнала: 2025, Номер 8(1)

Опубликована: Май 6, 2025

Язык: Английский

Процитировано

0
Enantioenriched BoronC,N‐Chelates via Chirality Transfer DOI Creative Commons
Yannick Stöckl,

Ethan J. Tait,

Wolfgang Frey

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(41)

Опубликована: Май 5, 2023

Molecules stereogenic only at tetrahedral boron atoms show great promise for applications, example as chiroptical materials, but are scarcely investigated due to their synthetic challenge. Hence, this study reports a two-step synthesis of enantioenriched C,N-chelates. First, the diastereoselective complexation alkyl/aryl borinates with chiral aminoalcohols furnished heterocycles in up 86 % yield and d.r. >98 : 2. Treatment these O,N-complexes chelate nucleophiles was surmised transfer stereoinformation via ate-complex into C,N-products. This chirality succeeded by substitution O,N-chelates lithiated phenyl pyridine give C,N-chelates 84 e.r. 97 3. The aminoalcohol ligands could be recovered after isolation tolerated alkyl, alkynyl (hetero-)aryl moieties further extended post-modification: transformations such catalytic hydrogenations or sequential deprotonation/electrophilic trapping were feasible while maintaining stereochemical integrity Structural aspects chelates studied variable temperature NMR X-ray diffraction.

Язык: Английский

Процитировано

6