Synthesis of Chiral 1,4-Oxazepane-5-Carboxylic Acids from Polymer-Supported Homoserine
The result's identifiers
Result code in 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>
Alternative codes found
RIV/61989592:15310/20:73603850
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Synthesis of Chiral 1,4-Oxazepane-5-Carboxylic Acids from Polymer-Supported Homoserine
Original language description
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.
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
—
Continuities
S - Specificky vyzkum na vysokych skolach
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
RSC Advances
ISSN
2046-2069
e-ISSN
—
Volume of the periodical
10
Issue of the periodical within the volume
NA
Country of publishing house
GB - UNITED KINGDOM
Number of pages
11
Pages from-to
35906-35916
UT code for WoS article
000574586100031
EID of the result in the Scopus database
2-s2.0-85093077142