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

Drabina, P., Sedlák, M., Růžička, A., Malkov, A. and Kočovský, P. (2008) 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. Tetrahedron: Asymmetry, 19(3), pp. 384-390. (doi: 10.1016/j.tetasy.2008.01.016)

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Abstract

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)pyridine s. Their complexes with Cu(I) catalyze the Kharash-Sosnovsky allylic oxidation with overall yields as high as 99% but with low enantioselectivity.

Item Type:Articles
Keywords:ACID ALLYLIC OXIDATION ASYMMETRIC KHARASCH REACTION CATALYSIS COMPLEX COMPLEXES COPPER-COMPLEXES CYCLOPROPANATION ENANTIOSELECTIVE ALLYLIC OXIDATION LIGANDS MECHANISM NMR-SPECTRA OLEFINS OXIDATION REMOVAL RING TERT-BUTYL PERBENZOATE
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Malkov, Dr Andrei and Kocovsky, Professor Pavel
Authors: Drabina, P., Sedlák, M., Růžička, A., Malkov, A., and Kočovský, P.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron: Asymmetry
Publisher:Elsevier
ISSN:0957-4166
ISSN (Online):1362-511X
Published Online:06 February 2008

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