Stereoselective Polymer-Supported Synthesis of Morpholine- and Thiomorpholine-3-carboxylic Acid Derivatives
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
- Klíčová slova
- amino acid, bromoketone, morpholine, nitrobenzenesulfonyl chloride, oxazine, solid-phase synthesis, stereoselective synthesis, thiazine, thiomorpholine,
- MeSH
- fluoreny chemie MeSH
- kyseliny karboxylové chemická syntéza chemie MeSH
- morfoliny chemická syntéza chemie MeSH
- oxaziny chemická syntéza chemie MeSH
- polymery chemie MeSH
- stereoizomerie MeSH
- techniky syntézy na pevné fázi metody MeSH
- thiaziny chemická syntéza chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- fluoreny MeSH
- kyseliny karboxylové MeSH
- morfoliny MeSH
- oxaziny MeSH
- polymery MeSH
- thiamorpholine MeSH Prohlížeč
- thiaziny MeSH
Herein we report the polymer-supported synthesis of 3,4-dihydro-2H-1,4-oxazine-3-carboxylic acid derivatives using immobilized Fmoc-Ser(tBu)-OH and Fmoc-Thr(tBu)-OH as the starting materials. After the solid-phase-synthesis of N-alkyl-N-sulfonyl/acyl intermediates, the target dihydrooxazines were obtained using trifluoroacetic acid-mediated cleavage from the resin. This approach was also studied for the preparation of dihydrothiazines from immobilized Fmoc-Cys(Trt)-OH. Inclusion of triethylsilane in the cleavage cocktail resulted in the stereoselective formation of the corresponding morpholine/thiomorpholine-3-carboxylic acids. Stereochemical studies revealed the specific configuration of the newly formed stereocenter and also the formation of stable N-acylmorpholine rotamers.
Citace poskytuje Crossref.org
Synthesis of chiral 1,4-oxazepane-5-carboxylic acids from polymer-supported homoserine
