Synthesis of Chiral 1,4-Oxazepane-5-Carboxylic Acids from Polymer-Supported Homoserine

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F20%3A73603850" target="_blank" >RIV/61989592:15110/20:73603850 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989592:15310/20:73603850

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlepdf/2020/ra/d0ra07997a" target="_blank" >https://pubs.rsc.org/en/content/articlepdf/2020/ra/d0ra07997a</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/D0RA07997A" target="_blank" >10.1039/D0RA07997A</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of Chiral 1,4-Oxazepane-5-Carboxylic Acids from Polymer-Supported Homoserine

Popis výsledku v původním jazyce

The preparation of novel 1,4-oxazepane-5-carboxylic acids bearing two stereocenters is reported in this article. Fmoc-HSe(TBDMS)-OH immobilized on Wang resin was reacted with different nitrobenzenesulfonyl chlorides and alkylated with 2-bromoacetophenones to yield N-phenacyl nitrobenzenesulfonamides. Their cleavage from the polymer support using trifluoroacetic acid (TFA) led to the removal of the silyl protective group followed by spontaneous lactonization. In contrast, TFA/triethylsilane (Et3SiH)-mediated cleavage yielded 1,4-oxazepane derivatives as a mixture of inseparable diastereomers. The regioselectivity/stereoselectivity depended on the substitution of the starting 2-bromoacetophenones and was studied in detail. Catalytic hydrogenation of the nitro group improved the separability of the resulting diastereomeric anilines, which allowed us to isolate and fully characterize the major isomers.

Název v anglickém jazyce

Synthesis of Chiral 1,4-Oxazepane-5-Carboxylic Acids from Polymer-Supported Homoserine

Popis výsledku anglicky

The preparation of novel 1,4-oxazepane-5-carboxylic acids bearing two stereocenters is reported in this article. Fmoc-HSe(TBDMS)-OH immobilized on Wang resin was reacted with different nitrobenzenesulfonyl chlorides and alkylated with 2-bromoacetophenones to yield N-phenacyl nitrobenzenesulfonamides. Their cleavage from the polymer support using trifluoroacetic acid (TFA) led to the removal of the silyl protective group followed by spontaneous lactonization. In contrast, TFA/triethylsilane (Et3SiH)-mediated cleavage yielded 1,4-oxazepane derivatives as a mixture of inseparable diastereomers. The regioselectivity/stereoselectivity depended on the substitution of the starting 2-bromoacetophenones and was studied in detail. Catalytic hydrogenation of the nitro group improved the separability of the resulting diastereomeric anilines, which allowed us to isolate and fully characterize the major isomers.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

RSC Advances

ISSN

2046-2069

e-ISSN

—

Svazek periodika

10

Číslo periodika v rámci svazku

NA

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

11

Strana od-do

35906-35916

Kód UT WoS článku

000574586100031

EID výsledku v databázi Scopus

2-s2.0-85093077142