Počet záznamů: 1
Diastereoselective Radical Couplings Enable the Asymmetric Synthesis of anti-β-Amino-α-hydroxy Carboxylic Acid Derivatives
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SYSNO ASEP 0495795 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Diastereoselective Radical Couplings Enable the Asymmetric Synthesis of anti-β-Amino-α-hydroxy Carboxylic Acid Derivatives Tvůrce(i) Hidasová, Denisa (UOCHB-X) ORCID
Janák, Martin (UOCHB-X)
Jahn, Emanuela (UOCHB-X) ORCID
Císařová, I. (CZ)
Jones, P. G. (DE)
Jahn, Ullrich (UOCHB-X) ORCIDZdroj.dok. European Journal of Organic Chemistry - ISSN 1434-193X
Roč. 2018, č. 37 (2018), s. 5222-5230Poč.str. 9 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova asymmetric synthesis ; oxygenation ; radical reactions ; tandem reactions ; total synthesis ; pure lithium amides ; conjugate addition Vědní obor RIV CC - Organická chemie Obor OECD Organic chemistry CEP GA13-40188S GA ČR - Grantová agentura ČR EF16_019/0000729 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000446662900016 EID SCOPUS 85054787764 DOI 10.1002/ejoc.201801139 Anotace anti-β-Amino-α-(aminoxy) esters or amides are synthesized by merging polar asymmetric aza-Michael additions of lithium 1-phenylethylamides to α,β-unsaturated carboxylic acid derivatives and diastereoselective radical couplings with the persistent free radical TEMPO mediated or catalyzed by ferrocenium hexafluorophosphate. Aliphatic α,β-unsaturated carboxylic derivatives gave good to excellent anti-diastereoselectivity for the radical coupling step, whereas the selectivity remained lower for cinnamic acid derivatives. The method allows the convenient introduction of a protected oxygen functionality, which is stable to acidic, basic, hydride and hydrogenolytic reductive conditions, but can be deprotected with zinc and acetic acid in the presence of TBDMS and Boc groups without noticeable epimerization. The tandem aza-Michael/oxygenation strategy was applied in total syntheses of the T(H)2 cytokine secretion modulator cytoxazone, and dipeptide fragments of the anti-β-amino-α-hydroxy acid containing macrocyclic peptides perthamide C and largamide H. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Rok sběru 2019
Počet záznamů: 1