Catalytic Enantioselective Reaction of α-Aminoacetonitriles Using Chiral Bis(imidazoline) Palladium Catalysts

Masaru Kondo; Tomoki Nishi; Tsubasa Hatanaka; Yasuhiro Funahashi; Shuichi Nakamura

doi:10.1002/anie.201503098

Catalytic Enantioselective Reaction of α-Aminoacetonitriles Using Chiral Bis(imidazoline) Palladium Catalysts

Angew Chem Int Ed Engl. 2015 Jul 6;54(28):8198-202. doi: 10.1002/anie.201503098. Epub 2015 May 27.

Authors

Masaru Kondo¹, Tomoki Nishi¹, Tsubasa Hatanaka², Yasuhiro Funahashi², Shuichi Nakamura³

Affiliations

¹ Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan) http://www.ach.nitech.ac.jp/∼organic/nakamura/index.html.
² Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043 (Japan).
³ Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan) http://www.ach.nitech.ac.jp/∼organic/nakamura/index.html. snakamur@nitech.ac.jp.

PMID: 26014509
DOI: 10.1002/anie.201503098

Abstract

The catalytic enantioselective reaction of diphenylmethylidene-protected α-aminoacetonitriles with imines has been developed. Good yields and diastereo- and enantioselectivities were observed for the reaction of various imines using chiral bis(imidazoline)/Pd catalysts. The reaction of α-aminonitriles with di-tert-butyl azodicarboxylate afforded chiral α,α-diaminonitriles in high yields with high enantioselectivities.

Keywords: asymmetric catalysis; diastereoselectivity; palladium; silver; synthetic methods.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aminoacetonitrile / chemistry*
Catalysis
Imidazolines / chemistry*
Models, Molecular
Palladium / chemistry*
Stereoisomerism

Substances

Imidazolines
Aminoacetonitrile
Palladium