bei Google ScholarTitelangaben
Fletcher, Matthew D. ; Harding, John R. ; Hughes, Rachael A. ; Kelly, Nicholas M. ; Schmalz, Holger ; Sutherland, Andrew ; Willis, Christine l.:
Three approaches to the synthesis of L-leucine selectively labelled with carbon-13 or deuterium in either diastereotopic methyl group.
In: Journal of the Chemical Society, Perkin Transactions 1.
(2000)
Heft 1
.
- S. 43-51.
ISSN 1364-5463
DOI: https://doi.org/10.1039/A907598D
Abstract
Three approaches to the synthesis of L-leucine selectively labelled with carbon-13 or deuterium in either diastereotopic methyl group as well as at C-3 and C-4 are described. In all three methods the stereogenic centre at C-2 was created with total stereocontrol via a one-pot, two-enzyme catalysed procedure involving hydrolysis and reductive amination of a 2-keto ester. However, the approaches vary in the synthesis of the isotopically labelled 2-keto esters and in the production of the stereogenic centre at C-4 which was achieved either via alkylation of a propionylated Evans’ auxiliary with labelled iodomethane or by the diastereoselective conjugate addition of a labelled organocopper reagent to crotonate tethered to a chiral sultam. The latter approach proved most efficient and using the (1R,2S,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethyldiphenyl)aminobornan-2-ol ester 27, [5-13C]-L-leucine was prepared with >98% de at C-4 and in 49% overall yield from the first labelled intermediate 28.
Weitere Angaben
| Publikationsform: | Artikel in einer Zeitschrift |
|---|---|
| Begutachteter Beitrag: | Ja |
| Institutionen der Universität: | Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Lehrstuhl Makromolekulare Chemie II Fakultäten Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie |
| Titel an der UBT entstanden: | Nein |
| Themengebiete aus DDC: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Eingestellt am: | 12 Dec 2019 10:11 |
| Letzte Änderung: | 12 Dec 2019 10:11 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/53570 |