Asymmetric Addition of Dimethylzinc to N-Tosylarylimines Catalyzed by a Rhodium−Diene Complex toward the Synthesis of Chiral 1-Arylethylamines
作者： Takahiro Nishimura , Yuichi Yasuhara , Tamio Hayashi
DOI: 10.1021/OL060213E
关键词:
摘要: A rhodium complex coordinated with a chiral diene, (R,R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (Ph-bod*), catalyzed the asymmetric addition of dimethylzinc to N-tosylarylimines give high yields 1-aryl-1-ethylamines enantioselectivity (94−98% ee).
acs.org
sci-hub.se 参考文章(33)
A. Cote, A. A. Boezio, A. B. Charette, Catalytic asymmetric addition of diorganozinc reagents to N-phosphinoylalkylimines Proceedings of the National Academy of Sciences of the United States of America. ,vol. 101, pp. 5405- 5410 ,(2004) , 10.1073/PNAS.0307096101
Norihito Tokunaga, Yusuke Otomaru, Kazuhiro Okamoto, Kazuhito Ueyama, Ryo Shintani, Tamio Hayashi, C2-Symmetric Bicyclo[2.2.2]octadienes as Chiral Ligands: Their High Performance in Rhodium-Catalyzed Asymmetric Arylation of N-Tosylarylimines Journal of the American Chemical Society. ,vol. 126, pp. 13584- 13585 ,(2004) , 10.1021/JA044790E
Alessandro A. Boezio, André B. Charette, Catalytic Enantioselective Addition of Dialkylzinc to N-Diphenylphosphinoylimines. A Practical Synthesis of α-Chiral Amines Journal of the American Chemical Society. ,vol. 125, pp. 1692- 1693 ,(2003) , 10.1021/JA027673X
Takao Saito, Tohru Yokozawa, Takero Ishizaki, Takashi Moroi, Noboru Sayo, Takashi Miura, Hidenori Kumobayashi, New Chiral Diphosphine Ligands Designed to have a Narrow Dihedral Angle in the Biaryl Backbone Advanced Synthesis & Catalysis. ,vol. 343, pp. 264- 267 ,(2001) , 10.1002/1615-4169(20010330)343:3<264::AID-ADSC264>3.0.CO;2-T
Christian Defieber, Jean-François Paquin, Sonia Serna, Erick M. Carreira, Chiral [2.2.2] Dienes as Ligands for Rh(I) in Conjugate Additions of Boronic Acids to a Wide Range of Acceptors Organic Letters. ,vol. 6, pp. 3873- 3876 ,(2004) , 10.1021/OL048240X
Jean-François Paquin, Christian Defieber, Corey R. J. Stephenson, Erick M. Carreira, Asymmetric synthesis of 3,3-diarylpropanals with chiral diene-rhodium catalysts. Journal of the American Chemical Society. ,vol. 127, pp. 10850- 10851 ,(2005) , 10.1021/JA053270W
Stefan Dahmen, Stefan Bräse, The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands. Journal of the American Chemical Society. ,vol. 124, pp. 5940- 5941 ,(2002) , 10.1021/JA025831E
Yusuke Otomaru, Asato Kina, Ryo Shintani, Tamio Hayashi, C2-Symmetric bicyclo[3.3.1]nona-2,6-diene and bicyclo[3.3.2]deca-2,6-diene: new chiral diene ligands based on the 1,5-cyclooctadiene framework Tetrahedron-asymmetry. ,vol. 16, pp. 1673- 1679 ,(2005) , 10.1016/J.TETASY.2005.02.022
Shū Kobayashi, Haruro Ishitani, Catalytic enantioselective addition to imines. Chemical Reviews. ,vol. 99, pp. 1069- 1094 ,(1999) , 10.1021/CR980414Z
Alexandre Côté, Alessandro A. Boezio, André B. Charette, Evidence for the Structure of the Enantioactive Ligand in the Phosphine-Copper-Catalyzed Addition of Diorganozinc Reagents to Imines Angewandte Chemie International Edition. ,vol. 43, pp. 6525- 6528 ,(2004) , 10.1002/ANIE.200461920