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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

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

Rok uplatnění

2018

Kód důvěrnosti údajů

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

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

—

Svazek periodika

neuveden

Číslo periodika v rámci svazku

37

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

5222-5230

Kód UT WoS článku

000446662900016

EID výsledku v databázi Scopus

2-s2.0-85054787764