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Diastereoselective Radical Couplings Enable the Asymmetric Synthesis of anti-beta-Amino-alfa-hydroxy Carboxylic Acid Derivatives

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F18%3A10381947" target="_blank" >RIV/00216208:11310/18:10381947 - isvavai.cz</a>

  • Result on the web

    <a href="https://doi.org/10.1002/ejoc.201801139" target="_blank" >https://doi.org/10.1002/ejoc.201801139</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/ejoc.201801139" target="_blank" >10.1002/ejoc.201801139</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Diastereoselective Radical Couplings Enable the Asymmetric Synthesis of anti-beta-Amino-alfa-hydroxy Carboxylic Acid Derivatives

  • Original language description

    anti-beta-Amino-alfa-(aminoxy) esters or amides are synthesized by merging polar asymmetric aza-Michael additions of lithium 1-phenylethylamides to alfa,beta-unsaturated carboxylic acid derivatives and diastereoselective radical couplings with the persistent free radical TEMPO mediated or catalyzed by ferrocenium hexafluorophosphate. Aliphatic alfa,beta-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-beta-Amino-alfa-hydroxy acid containing macrocyclic peptides perthamide C and largamide H.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10401 - Organic chemistry

Result continuities

  • Project

  • Continuities

    Z - Vyzkumny zamer (s odkazem do CEZ)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2018

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    European Journal of Organic Chemistry

  • ISSN

    1434-193X

  • e-ISSN

  • Volume of the periodical

    neuveden

  • Issue of the periodical within the volume

    37

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    9

  • Pages from-to

    5222-5230

  • UT code for WoS article

    000446662900016

  • EID of the result in the Scopus database

    2-s2.0-85054787764