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Asymmetric Addition of Alkyllithium to Chiral Imines:  α-Naphthylethyl Group as a Chiral Auxiliary

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posted on 1999-11-09, 00:00 authored by Hideki Yamada, Tomohiko Kawate, Atsushi Nishida, Masako Nakagawa
The diastereoselective nucleophilic addition of alkyllithium to N-alkylidene-α-naphthylethylamine was carried out. In the presence of Lewis acids or Lewis bases, organolithiums reacted smoothly with imines to give the corresponding amines in high stereoselectivity (up to 100% de). Furthermore, the resulting optically active amines were found to be useful for asymmetric reactions as chiral ligands.

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