Literature DB >> 27093481

Visible-Light Photoredox Synthesis of Chiral α-Selenoamino Acids.

Min Jiang1, Haijun Yang1, Hua Fu1.   

Abstract

N-Acetoxyphthalimide derivatives of two genetically coded proteinogenic amino acids, l-aspartic acid and glutamic acid, were used as visible light photoredox chiral sources and radical precursors, diorganyl diselenides were used as the radical acceptors, and the diverse chiral α-selenoamino acid derivatives were prepared in good yields at room temperature. Furthermore, decarboxylative coupling of N-protected dipeptide active ester with diphenyl diselenide provided the corresponding selenodipeptide. The simple protocol, mild reaction conditions, high efficiency, and chiral keeping of this method make it an important strategy for the synthesis of chiral molecules.

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Year:  2016        PMID: 27093481     DOI: 10.1021/acs.orglett.6b00489

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

Review 1.  Photocatalytic Modification of Amino Acids, Peptides, and Proteins.

Authors:  Cecilia Bottecchia; Timothy Noël
Journal:  Chemistry       Date:  2018-11-05       Impact factor: 5.236

2.  Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions.

Authors:  Jing-Yu Guo; Ze-Yu Zhang; Ting Guan; Lei-Wen Mao; Qian Ban; Kai Zhao; Teck-Peng Loh
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

3.  Olefination of Alkyl Halides with Aldehydes by Merging Visible-Light Photoredox Catalysis and Organophosphorus Chemistry.

Authors:  Min Jiang; Haijun Yang; Quentin Lefebvre; Jihu Su; Hua Fu
Journal:  iScience       Date:  2018-07-20

Review 4.  Radical-Based Synthesis and Modification of Amino Acids.

Authors:  Francisco José Aguilar Troyano; Kay Merkens; Khadijah Anwar; Adrián Gómez-Suárez
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-04       Impact factor: 15.336

  4 in total

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