Synthesis of optically active atropisomeric anilide derivatives through diastereoselective N-allylation with a chiral Pd-pi-allyl catalyst

Osamu Kitagawa; Masashi Takahashi; Mitsuteru Kohriyama; Takeo Taguchi

doi:10.1021/jo035305l

Synthesis of optically active atropisomeric anilide derivatives through diastereoselective N-allylation with a chiral Pd-pi-allyl catalyst

J Org Chem. 2003 Dec 12;68(25):9851-3. doi: 10.1021/jo035305l.

Authors

Osamu Kitagawa¹, Masashi Takahashi, Mitsuteru Kohriyama, Takeo Taguchi

Affiliation

¹ Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.

PMID: 14656123
DOI: 10.1021/jo035305l

Abstract

N-Allylation of o-tert-butyl anilides derived from o-tert-butyl aniline and (S)-lactic acid or (S)-mandelic acid proceeded with high diastereoselectivity in the presence of a (BINAP)Pd-pi-allyl catalyst to give atropisomeric N-allyl o-tert-butyl anilide derivatives.