Amination of Benzoxazoles by Visible-Light Photoredox Catalysis

Wang, Jia-Di; Liu, Yu-Xia; Duan, Xue; Wang, Chao; Xiao, Jianliang

doi:10.1055/s-0034-1378325

Cited by 29 publications

(2 citation statements)

References 3 publications

(5 reference statements)

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“…[8][9][10]53] In addition, 1,3dipolar cycloaddition between the metallated azomethine ylide and the ketone intermediate is another non-negligible chemoselectivity challenge. [54]…”

Section: Introductionmentioning

confidence: 99%

Copper/Ruthenium Relay Catalysis for Stereodivergent Access to δ‐Hydroxy α‐Amino Acids and Small Peptides

Fu,

He,

Chang

et al. 2024

Angewandte Chemie

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An atom‐ and step‐economic and redox neutral cascade reaction enabled by asymmetric bimetallic relay catalysis via merging ruthenium‐catalyzed asymmetric borrowing‐hydrogen reaction with copper‐catalyzed asymmetric Michael addition has been realized. A variety of highly functionalized 2‐amino‐5‐hydroxyvaleric acid esters or peptides bearing 1,4‐nonadjacent stereogenic centers have been prepared in high yields with excellent enantio‐ and diastereoselectivity. Judicious selection and rational modification of the Ru‐catalysts with careful tuning reaction conditions played a pivotal role in stereoselectivity control as well as attenuating undesired α‐epimerization, thus enabling a full complement of all four stereoisomers that were otherwise inaccessible in previous work. Concise asymmetric stereodivergent synthesis of the key intermediates for biologically important chiral molecules further showcases the synthetic utility of this methodology.

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“…[8][9][10]53] In addition, 1,3dipolar cycloaddition between the metallated azomethine ylide and the ketone intermediate is another non-negligible chemoselectivity challenge. [54]…”

Section: Introductionmentioning

confidence: 99%

Copper/Ruthenium Relay Catalysis for Stereodivergent Access to δ‐Hydroxy α‐Amino Acids and Small Peptides

Fu,

He,

Chang

et al. 2024

Angewandte Chemie

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show abstract

“…8 In 2014, Xiao's group reported the amination reaction of benzoxazole and amines. 9 The target product was obtained from benzoxazole and the in situ generated chloramine by using [Ir(dtbpy)(ppy) 2 ]PF 6 as a photocatalyst and Ph 3 N as an additive under 3 W blue light irradiation for 60 h (Scheme 1c). In this elegant photocatalytic strategy, the expensive Ir-photocatalyst and a long reaction time are still required for good reaction yields.…”

Section: Introductionmentioning

confidence: 99%