Kinetic resolution of 1,1'-binaphthyl-2,2'-diamine derivatives by chiral calcium phosphate-catalyzed acylation

Tatsuhiro Uchikura; Yuki Kanno; Yukino Fukuda; Mikoto Sato; Takahiko Akiyama

doi:10.1039/d4ob00355a

Kinetic resolution of 1,1'-binaphthyl-2,2'-diamine derivatives by chiral calcium phosphate-catalyzed acylation

Org Biomol Chem. 2024 May 1;22(17):3444-3447. doi: 10.1039/d4ob00355a.

Authors

Tatsuhiro Uchikura¹, Yuki Kanno¹, Yukino Fukuda¹, Mikoto Sato¹, Takahiko Akiyama¹

Affiliation

¹ Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, Japan. takahiko.akiyama@gakushuin.ac.jp.

PMID: 38595221
DOI: 10.1039/d4ob00355a

Abstract

1,1'-Binaphthyl-2,2'-diamine (BINAM) is a useful axially chiral compound. The kinetic resolution of BINAM is one of the most crucial methods for synthesizing chiral BINAM. We have developed a chiral calcium phosphate-catalyzed kinetic resolution of BINAM by utilizing an acylation reaction to produce a mono-amide. The kinetic resolution of BINAM derivatives was achieved by using isobutyric anhydride in the presence of chiral calcium phosphate and 4-morpholinopyridine with up to s = 127. 6,6'-Substituted BINAM derivatives were also applicable for this reaction. The resulting mono-acylated BINAM could be transformed into BINAM by hydrolysis under acidic conditions.