First Application of Optically Active trans-1,2-Bis(2- Aminophenyl) cyclopentane for Asymmetric Reaction: Enantioselective N-Acetylation of Secondary Alkyl Amines

Chinese Chemical Letters

Volumn 12, Issue 1, 2001, Pages 1-4

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

^a SICHUAN UNIVERSITY   (China)

^b TOHO UNIVERSITY   (Japan)

Author keywords

Chiral; Enantioselective N acetylation

Indexed keywords

EID: 0035584640     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (8)

1. C. S. Chen, C. J. Sih Angew. Chem., Int. Ed. Engl. 1989, 28, 695. G. Asensio, C. Andreu, J. A. Marco Tetrahedron Lett. 1991, 32, 4197. E. I. Luis, M. S. Víctor, R. Francisca, G. Vicente Tetrahedron: Asymmetry 1997, 8, 2675.
2. C. S. Chen, C. J. Sih Angew. Chem., Int. Ed. Engl. 1989, 28, 695. G. Asensio, C. Andreu, J. A. Marco Tetrahedron Lett. 1991, 32, 4197. E. I. Luis, M. S. Víctor, R. Francisca, G. Vicente Tetrahedron: Asymmetry 1997, 8, 2675.
3. C. S. Chen, C. J. Sih Angew. Chem., Int. Ed. Engl. 1989, 28, 695. G. Asensio, C. Andreu, J. A. Marco Tetrahedron Lett. 1991, 32, 4197. E. I. Luis, M. S. Víctor, R. Francisca, G. Vicente Tetrahedron: Asymmetry 1997, 8, 2675.
4. K. Kondo, T. Kurosaki, Y. Murakami Synlett 1998, 725.
5. J. S. Yang, K. Kondo, Y. Murakami Coll. Czech. Chem. Comm. 2000, 65, 549.
6. Quite recently, Fu has reported an effective planar-chiral reagent for enantioselective N-acetylation: Y. Ie, G. C. Fu Chem. Commun. 2000, 119.
7. 4: C 71.41%; H 6.71%; N 6.66%. Found: C 71.41%; H 6.73%; N 6.81%.
8. The recovery yields and ee values of the unreacted starting amines were as follows: 4 (69%, 3% ee): 5 (71%, 4% ee); 6 (72%, 3% ee); 7 (68%, 7% ee); 8 (64%, 1% ee).