AN UNUSUAL REARRANGEMENT OF N,N-DIBENZYL-2-AMINOPROPANAL TO N,N-DIBENZYL-1-AMINOPROPANONE

Authors
ADIA M HENAFF N WHITING A
Citation
M. Adia et al., AN UNUSUAL REARRANGEMENT OF N,N-DIBENZYL-2-AMINOPROPANAL TO N,N-DIBENZYL-1-AMINOPROPANONE, Tetrahedron letters, 38(17), 1997, pp. 3101-3102
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
17
Year of publication
1997
Pages
3101 - 3102
Database
ISI
SICI code
0040-4039(1997)38:17<3101:AURONT>2.0.ZU;2-J
Abstract
N,N-dibenzyl-2-aminopropanal la derived from alanine rearranges to the corresponding ketone, N,N-dibenzyl-1-aminopropanone upon exposure to either silica gel or pyridinium acetate. Similar rearrangements do not occur with aldehydes derived from phenylalinine, valine, leucine, pro line or phenylglycine. One mechanistic explanation for the rearrangeme nt is a facile 1,2-methyl shift, followed by 12-hydrogen shift. (C) 19 97 Elsevier Science Ltd.