Enantiomerically enriched (R)- and (S)-alpha-methylphenylalanine via asymmetric PTC C-alkylation catalysed by NOBIN

Authors
Belokon', YN Kochetkov, KA Churkina, TD Ikonnikov, NS Vyskocil, S Kagan, HB
Citation
Yn. Belokon' et al., Enantiomerically enriched (R)- and (S)-alpha-methylphenylalanine via asymmetric PTC C-alkylation catalysed by NOBIN, TETRAHEDR-A, 10(9), 1999, pp. 1723-1728
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
9
Year of publication
1999
Pages
1723 - 1728
Database
ISI
SICI code
0957-4166(19990507)10:9<1723:EE(A(V>2.0.ZU;2-D
Abstract
Enantiopure 2-hydroxy-2'-amino-1,1'-binaphthyl (NOBIN) is shown to catalyse C-alkylation of aldimine Schiff's bases of alanine ester under phase-trans fer catalysis conditions (solid NaOH or NaH, toluene, ambient temperature, 10% NOBIN). Using (R)-NOBIN, the final (S)-alpha-methylphenylalanine was ob tained in up to 68% ee. (C) 1999 Published by Elsevier Science Ltd. All rig hts reserved.