Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction

Osamu Kitagawa; Masashi Takahashi; Masatoshi Yoshikawa; Takeo Taguchi

doi:10.1021/ja042216x

Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction

J Am Chem Soc. 2005 Mar 23;127(11):3676-7. doi: 10.1021/ja042216x.

Authors

Osamu Kitagawa¹, Masashi Takahashi, Masatoshi Yoshikawa, Takeo Taguchi

Affiliation

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

PMID: 15771484
DOI: 10.1021/ja042216x

Abstract

In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, N-arylation of ortho-tert-butyl-NH-anilides with 4-nitroiodobenzene proceeds with high enantioselectivity (89-95% ee) to give optically active atropisomeric anilides possessing N-C chiral axis. Furthermore, the intramolecular version of the present catalytic asymmetric N-arylation gave atropisomeric lactams with high optical purity (94-96% ee).