Catalytic Enantioselective Reaction of Allenylnitriles with Imines Using Chiral Bis(imidazoline)s Palladium(II) Pincer Complexes

Masaru Kondo; Masashi Omori; Tsubasa Hatanaka; Yasuhiro Funahashi; Shuichi Nakamura

doi:10.1002/anie.201702429

Catalytic Enantioselective Reaction of Allenylnitriles with Imines Using Chiral Bis(imidazoline)s Palladium(II) Pincer Complexes

Angew Chem Int Ed Engl. 2017 Jul 17;56(30):8677-8680. doi: 10.1002/anie.201702429. Epub 2017 Jun 19.

Authors

Masaru Kondo^{1

2}, Masashi Omori¹, Tsubasa Hatanaka³, Yasuhiro Funahashi³, Shuichi Nakamura^{1

2}

Affiliations

¹ Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
² Frontier Research Institute for Material Science, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
³ Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan.

PMID: 28628262
DOI: 10.1002/anie.201702429

Abstract

The first highly enantioselective reaction of allenylnitriles with imines has been developed. Excellent yields and enantioselectivities were observed for the reaction with various imines using chiral Phebim-Pd^II complexes. This process offers a simple and efficient synthetic route for various functionalized α-vinylidene-β-aminonitriles and their derivatives.

Keywords: Lewis acids; allenyl compounds; asymmetric synthesis; pincer complex.

Publication types

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