Design, synthesis, and optical resolution of a novel non-natural chiral auxiliary, 1-(2,5-dimethoxyphenyl)ethylamine. Application to diastereoselective alkylation of aldimines

Tetrahedron

Volumn 55, Issue 21, 1999, Pages 6453-6464

  Kohara, Takehiro ^a   Hashimoto, Yukihiko ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Alkylation; Chelation; Diastereoselection; Imines

Indexed keywords

1 (2,5 DIMETHOXYPHENYL)ETHYLAMINE; IMINE; UNCLASSIFIED DRUG;

ACETYLATION; ALKYLATION; ARTICLE; CHELATION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; OPTICAL RESOLUTION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033591148     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00307-5     Document Type: Article

References (33)

1. Herrmann R. Stereoselective Synthesis: Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, editors. Methods of the Organic Chemistry 4th Edition, vol. E 21f. Stuttgart-New York: Thime, 1996:5759-6001.
2. Seyden-Penne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis. New York: John Wiley, 1995:43-85.
3. Newman P. Optical Resolution Procedures for Chemical Compounds. Optical Resolution Information Center, Manhattan College, New York: Riverdale, 1981.
4. Juaristi E, Escalante J, León-Romo JL, Reyes A. Tetrahedron: Asymmetry. 1998;9:715-740.
5. Morrison JD. Asymmetric Synthesis. New York: Academic Press, 1983.
6. Sivova LI, Sivov NA, Gracheva RA, Potapov VM. J. Org. Chem. USSR. 1978;14:731-735.
7. Boga C, Savoia D, Umani-Ronchi A. Tetrahedron: Asymmetry. 1990;1:291-294.
8. Alvaro G, Savoia D, Valentinetti MR. Tetrahedron. 1996;52:12571-12586.
9. Hashimoto Y, Kai A, Saigo K. Tetrahedron Lett. 1995;36:8821-8824.
10. Volkmann RA. Comprehensive Organic Synthesis: Trost BM, Fleming I, editors. Oxford: Pergamon Press, 1991:355-396.
11. Risch R, Arend M. Stereoselective Synthesis: Helmchen G, Hoffmann RW, Mulzer J, Schaumann E, editors. Methods of The Organic Chemistry 4th Edition, vol. E 21b. Stuttgart-New York: Thime, 1996:1833-1907.
12. Enders D, Reinhold U. Tetrahedron: Asymmetry. 1997;8:1895-1946.
13. Bloch R. Chem. Rev. 1998;98:1407-1438.
14. Saigo K, Ogawa S, Kikuchi S, Kasahara A, Nohira H. Bull. Chem. Soc. Jpn. 1982;55:1568-1573.
15. Sudo A, Hashimoto Y, Kimoto H, Hayashi K, Saigo K. Tetrahedron: Asymmetry. 1994;5:1333-1346.
16. Sudo A, Matsumoto M, Hashimoto Y, Saigo K. Tetrahedron: Asymmetry. 1995;6:1853-1856.
17. Sudo A, Saigo K. Tetrahedron: Asymmetry. 1995;6:2153-2156.
18. Saigo K, Sudo A, Hashimoto Y. J. Synth. Org. Chem., Jpn. 1998;56:386-394.
19. Hashimoto Y, Kobayashi N, Kai A, Saigo K. Synlett. 1995:961-962.
20. Kinbara K, Sakai K, Hashimoto Y, Nohira H, Saigo K. Tetrahedron: Asymmetry. 1996;7:1539-1542.
21. Yamamoto Y, Komatsu T, Maruyama K. J. Am. Chem. Soc. 1984;106:5031-5033.
22. Yamamoto Y, Nishii S, Maruyama K, Komatsu T, Ito W. J. Am. Chem. Soc. 1986;108:7778-7786.
23. Beuchet P, Marrec NL, Mosset P. Tetrahedron Lett. 1992;33:5959-5960.
24. Gao Y, Sato F. J. Org. Chem. 1995;60:8136-8137.
25. Wang D, Dai L, Hou X. Tetrahedron Lett. 1995;36:8649-8652.
26. Wang D, Dai L, Hou X, Zhang Y. Tetrahedron Lett. 1996;37:4187-4188.
27. Alvaro G, Boga C, Savoia D, Umani-Ronchi A. J. Chem. Soc., Perkin Trans. 1. 1996:875-882.
28. Alvaro G, Pacioni P, Savoia D. Chem. Eur. J. 1997;3:726-731.
29. Bringmann G, Geisler JP, Geuder T, Künkel G, Kinzinger L. Liebigs Ann. Chem. 1990:795-805.
30. Chelucci G, Cabras MA, Saba A. Tetrahedron: Asymmetry. 1994;5:1973-1978.
31. Hirao A, Hattori I, Yamaguchi K, Nakahama S. Synthesis. 1982:461-462.
32. Ingersoll AW. Org. Synth., Coll.,vol. 2. New York: John Wiley, 1966:503-506.
33. Brown E, Moudachirou M. Tetrahedron. 1994;50:10309-10320.