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

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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-05, Vol.22 (17), p.3444-3447
Main Authors: Uchikura, Tatsuhiro, Kanno, Yuki, Fukuda, Yukino, Sato, Mikoto, Akiyama, Takahiko
Format: Article
Language:English
Subjects:
Acylation
Calcium
Calcium phosphates
Diamines
Phosphates
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Summary: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. Chiral calcium phosphate-catalyzed kinetic resolution of BINAM derivatives.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00355a