ALPHA-ALKYLATION OF ALPHA-AMINO ESTERS BY USING A PYRIDOXAL MODEL-COMPOUND HAVING A LI-IONOPHORE CHARACTER()

Authors
MIYASHITA K MIYABE H KUROZUMI C TAI K IMANISHI T
Citation
K. Miyashita et al., ALPHA-ALKYLATION OF ALPHA-AMINO ESTERS BY USING A PYRIDOXAL MODEL-COMPOUND HAVING A LI-IONOPHORE CHARACTER(), Tetrahedron, 52(37), 1996, pp. 12125-12136
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
37
Year of publication
1996
Pages
12125 - 12136
Database
ISI
SICI code
0040-4020(1996)52:37<12125:AOAEBU>2.0.ZU;2-H
Abstract
Synthesis of alpha,alpha-dialkyl-alpha-amino esters by alpha-alkylatio n of aldimines prepared from a novel pyridoxal model compound was stud ied. The alpha-alkylation of the aldimines having an ethoxy-ethoxy gro up at C-3 proceeded most rapidly when LIOH was employed as a base and gave alpha,alpha-dialkyl-alpha-amino esters after acidic hydrolysis. T he chelated structure composed of the aldimine and Li+ was also reveal ed by H-1-NMR analysis. Copyright (C) 1996 Elsevier Science Ltd