Synthesis and resolution of a new C2-symmetric chiral bis-aniline, trans-1,2-bis(2-aminophenyl)cyclopentane

Collection of Czechoslovak Chemical Communications

Volumn 65, Issue 4, 2000, Pages 549-554

  Yang, Jin Song ^a   Kondo, Kazuhiro ^a   Murakami, Yasuoki ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

Amines; Asymmetric catalysis; Axial chirality; C2 symmetry; Chiral bis anilines; N ligand

Indexed keywords

EID: 0034344092     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20000549     Document Type: Article

References (12)

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4. c) Reetz M. T., Bohres E., Goddard R.: Chem. Commun. 1998, 935;
5. d) Kondo K., Kurosaki T., Murakami Y.: Synlett 1998, 725;
6. e) Suga H., Fudo T., Ibata T.: Synlett 1998, 933;
7. f) Nishida A., Yamanaka M., Nakagawa M.: Tetrahedron Lett. 1999, 40, 1555.
8. Stewart J. J. P.: J. Comput. Chem. 1989, 10, 209.
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11. For preparation of ligand 5, see: Kranenburg M., van der Burgt Y. E. M., Kamer P. C. J., van Leeuwen P. W. N. M., Goubitz K., Fraanje J.: Organometallics 1995, 14, 3081.
12. By shortening the time of palladium-catalyzed reaction from 20 to 9 h, the Buchwald amination of (1S,2S)-4 was carried out to afford (1S,2S)-2 in 4% yield with 95% ee, along with the mono-aniline 11 in 19% yield and the starting bis-triflate 4 in 45% yield (see below).