Computational studies of effective asymmetric alkylation utilizing a chiral Schiff base derived from 2-hydroxy-3-pinanone - Part 1

Tetrahedron

Volumn 52, Issue 16, 1996, Pages 5961-5970

  Matsumoto, Takatoshi ^a,b   Shioiri, Takayuki ^a   Osawa, Eiji ^b  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

THIAZOLE DERIVATIVE;

ALKYLATION; ARTICLE; COMPUTER SIMULATION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029885667     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00226-8     Document Type: Article

References (23)

1. (a) Yamada, S.; Oguri, T.; Shioiri, T. J. Chem. Soc. Chem. Commun., 1976, 136.,
2. (b) Oguri, T.; Kawai, N.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull., 1978, 26, 803.
3. (a) Irako, N.; Hamada, Y.; Shioiri, T. Presented in part at the 113th Annual Meeting of the Pharmaceutical Society of Japan, Osaka, March, 1993, Abstracts of Papers 2, 135.,
4. (b) Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron, 1995, 51, 12731 and references therein.
5. MOPAC 93.00, Stewart, J. J. P., Fujitsu Ltd., Tokyo, Japan, 1993. Available from Quantum Chemistry Program Exchange, University of Indiana, Bloomington, IN.
6. Anders, E.; Koch, R.; Freunscht, P. J. Comput. Chem., 1993, 14, 1301.
7. (a) CA Index Guide, Appendix IV, 1992, P202-203.,
8. (b) International Union of Pure and Applied Chemistry, Nomenclature of Organic Chemistry, Section A, B, C, D, E, F, and H, 1979ed., Pergmon Press, Oxford (England) 1979, Section E and Appendix 2, P473-490.
9. (a) Jemmis, E. D.; Schleyer, P. v. R. J. Am. Chem. Soc., 1982, 104, 4781.,
10. (b) Neugebauer, W.; Clark, T.; Schleyer, P. v. R. Chem. Ber., 1983, 116, 3282.,
11. (c) Jiao, H.; Schleyer, P. v. R. Angew. Chem. Int. Ed. Engl., 1993, 32, 1760.,
12. (d) Jiao, H.; Schleyer, P. v. R. J. Chem Soc. Faraday Trans., 1994, 90, 1559.
13. (a) Neugebauer, W.; Kos, A. J.; Schleyer, P. v. R. J. Organomet. Chem., 1982, 228, 107.,
14. (b) Wilhelm, D.; Clark, T.; Schleyer, P. v. R. J. Chem. Soc. Chem. Commun., 1983, 211.,
15. (c) Wilhelm, D.; Clark, T.; Schleyer, P.v. R.; Courtneidge, J. L.; Davies, A. G. J. Am. Chem. Soc., 1984, 106, 361.,
16. (d) Schleyer, P. v. R.; Clark, T.; Kos, A. J.; Spitznagel, G. W.; Rohde, C.; Ared, D.; Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc., 1984, 106, 6467.
17. (a) Paquette, L. A.; Bauer, W.; Sivik, M. R.; Bühl, M.; Feigel, M.; Schleyer, P. v. R. J. Am. Chem. Soc., 1990, 112, 8776.,
18. (b) Reich, H. J.; Borst, J. P. J. Am. Chem. Soc., 1991, 113, 1835.,
19. (c) Bauer, W.; O'Doherty, G. A.; Schleyer, P. v. R.; Paquette, L. A. J. Am. Chem. Soc., 1991, 113, 7093.,
20. (d) Bauer, W.; Sivik, M. R.; Friedrich, D.; Schleyer, P. v. R.; Paquette, L. A. Organometallics, 1992, 11, 4178.
21. This charge distribution was calculated by ESP ( Electrostatic Potential) method. (a) Besler, B. H.; Merz, Jr, K. M.; Kollman, P. A. J. Comp. Chem., 1990, 11, 431.,
22. (b) MOPAC 93 Manual.
23. Matsumoto, T.; Shioiri, T.; Osawa, E. Tetrahedron, the following paper.