Asymmetric addition of Grignard reagents to chiral 1-acylpyridinium salts: A chiral auxiliary study

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3807-3810

  Comins, Daniel L ^a   Guerra Weltzien, Lourdes ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ORGANIC CHEMISTRY;

EID: 0029893402     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00709-5     Document Type: Article

References (19)

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2. (b) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
3. (a) Comins, D. L.; Hong, H. J. Am. Chem. Soc. 1993, 115, 8851.
4. (b) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035.
5. (a) Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794 and references cited therein.
6. (b) Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press, Inc.: Greenwich, Vol. 2, in press.
7. (a) Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908.
8. (b) Whitesell, J. K.; Liu, C. L.; Buchanan, C. M.; Chen, H.-H.; Minton, M. A. J. Org. Chem. 1986, 51, 551.
9. (c) d'Angelo, J.; Maddaluno, J. J. Am. Chem. Soc. 1986, 108, 8112.
10. For an excellent review on cyclohexyl-based chiral auxiliaries, see: Whitesell, J. K. Chem. Rev. 1992, 92, 953.
11. (a) Comins, D. L.; Salvador, J. M. Tetrahedron Lett. 1993, 34, 801.
12. (b) Comins, D. L.; Salvador, J. M. J. Org. Chem. 1993, 58, 4656.
13. Comins, D. L.; Guerra-Weltzien, L.; Salvador, J. M. Synlett 1994, 972.
14. Whitesell, J. K.; Carpenter, J. F.; Yaser, H. K.; Machajewski, T. J. Am. Chem. Soc. 1990, 112, 7653.
15. (a) Mezrhab, B.; Dumas, F.; d'Angelo, J.; Riche, C. J. Org. Chem. 1994, 59, 500.
16. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
17. (a) Singh, P.; Comins, D. L.; Joseph, S. P. Acta Crystallogr. 1994, C50, 25.
18. (b) For a review on π stacking effects in asymmetric synthesis, see: Jones, G. B.; Chapman, B. J. Synthesis 1995, 475.
19. For a semiempirical theoretical study of intramolecular π-stacking and asymmetric induction, see: Maddaluno, J. F.; Gresh, N.; Giessner-Prettre, C. J. Org. Chem. 1994, 59, 793.