Synthesis of chiral 1,4-oxazepane-5-carboxylic acids from polymer-supported homoserine
Status PubMed-not-MEDLINE Jazyk angličtina Země Anglie, Velká Británie Médium electronic-ecollection
Typ dokumentu časopisecké články
PubMed
35517075
PubMed Central
PMC9056997
DOI
10.1039/d0ra07997a
PII: d0ra07997a
Knihovny.cz E-zdroje
- Publikační typ
- časopisecké články MeSH
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.
Department of Organic Chemistry Faculty of Science Palacký University 771 46 Olomouc Czech Republic
JEOL Ltd JEOL House Silver Court Watchmead Welwyn Garden City Hertfordshire AL7 1LT UK
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