Diastereoselective Radical Couplings Enable the Asymmetric Synthesis of anti-β-Amino-α-hydroxy Carboxylic Acid Derivatives
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00495795" target="_blank" >RIV/61388963:_____/18:00495795 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201801139" target="_blank" >http://dx.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-β-Amino-α-hydroxy Carboxylic Acid Derivatives
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
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
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Volume of the periodical
2018
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