Asymmetric addition of alkyllithium to chiral imines: alpha-Naphthylethyl group as a chiral auxiliary

Authors
Yamada, H Kawate, T Nishida, A Nakagawa, M
Citation
H. Yamada et al., Asymmetric addition of alkyllithium to chiral imines: alpha-Naphthylethyl group as a chiral auxiliary, J ORG CHEM, 64(24), 1999, pp. 8821-8828
Citations number
75
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
24
Year of publication
1999
Pages
8821 - 8828
Database
ISI
SICI code
0022-3263(19991126)64:24<8821:AAOATC>2.0.ZU;2-Y
Abstract
The diastereoselective nucleophilic addition of alkyllithium to N-alkyliden e-alpha-naphthylethylamine was carried out. In the presence of Lewis acids or Lewis bases, organolithiums reacted smoothly with imines to give the cor responding amines in high stereoselectivity (up to 100% de). Furthermore, t he resulting optically active amines were found to be useful for asymmetric reactions as chiral ligands.