Synthesis of (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides and (R)- and (S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines
ČlánekOtevřený přístuppeer-reviewedpostprintDatum publikování
2008
Vedoucí práce
Oponent
Název časopisu
Název svazku
Vydavatel
Elsevier
Abstrakt
Both (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides have been prepared by the reductive benzylation of (R)- and (S)-2-amino-2,3-dimethylbutanamides, followed by reductive methylation and hydrogenolytic removal of the benzyl group. The reductive benzylation is chemoselective, and not accompanied by dibenzylation even with the application of excess benzaldehyde. Acylation of the (R)- and (S)-2-N-methylamino-2,3-dimethylbutanamides with picolinic acid and subsequent ring closure gave the respective (R)- and (S)-(5-isopropyl-1,5-dimethyl-4,5-dihydro-1H-imidazol-4-on-2-yl)pyridines. Their complexes with Cu(I) catalyze the Kharash–Sosnovsky allylic oxidation with overall yields as high as 99% but with low enantioselectivity.
Rozsah stran
p. 384-390
ISSN
0957-4166
Trvalý odkaz na tento záznam
Projekt
Zdrojový dokument
Tetrahedron Asymmetry. 2008, vol. 19, issue 3
Vydavatelská verze
http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THT-4RS9SKW-C&_user=640852&_coverDate=02%2F19%2F2008&_rdoc=1&_fmt=high&_orig=search&_origin=search&_sort=d&_docanchor=&view=c&_acct=C000032310&_version=1&_urlVersion=0&_userid=640852&md5=31863495d361cc8e2ba2179cfb15b497&searchtype=a
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open access