Asymmetric Lewis Acid-Catalyzed Diels-Alder Reactions of α,β-Unsaturated Ketones and α,β-Unsaturated Acid Chlorides

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4293-4295

  Hawkins, Joel M ^a,b   Nambu, Mitch ^a,b   Loren, Stefan ^a,b  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; LEWIS ACID;

ARTICLE; BINDING SITE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; DIELS ALDER REACTION; MATHEMATICAL COMPUTING;

EID: 0344496838     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035524t     Document Type: Article

References (15)

1. For a detailed discussion, see: Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 11, 2458.
2. For the preferential coordination of electronically differentiated substituted benzophenone lone pairs allowing maximum π-electron donation in an asymmetric reduction system, see: Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 36, 9153.
3. 1
4. Corey recently described an enantioselective Lewis acid-catalyzed Diels-Alder reaction with ethyl vinyl ketone: Ryu, D. H.; Lee, T. L.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992. Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388.
5. Corey recently described an enantioselective Lewis acid-catalyzed Diels-Alder reaction with ethyl vinyl ketone: Ryu, D. H.; Lee, T. L.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992. Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388.
6. Hawkins, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794.
7. Hawkins, J. M.; Loren, S.; Nambu, M. J. Am. Chem. Soc. 1994, 116, 1657.
8. 4
9. Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127.
10. 13C NMR, and high-resolution mass spectra. Acid chloride reactions were quenched with an excess of 25% TEA/methanol to give the corresponding methyl esters.
11. Cyclohexadiene reacts considerably slower than cyclopentadiene with methyl vinyl ketone under the conditions of Table 1.
12. 3, see: Rasmussen, S. E.; Broch, N. C. Acta Chem. Scand. 1966, 20, 1351 (benzoyl chloride). Chevrier, P. B.; Le Carpentier, J.-M.; Weiss, R. Acta Crystallogr. B 1972, 28, 2659 (toluoyl chlorides). Le Carpentier, J.-M.; Weiss, R. Acta Crystallogr. B 1972, 28, 1437 (propionyl chloride).
13. 3, see: Rasmussen, S. E.; Broch, N. C. Acta Chem. Scand. 1966, 20, 1351 (benzoyl chloride). Chevrier, P. B.; Le Carpentier, J.-M.; Weiss, R. Acta Crystallogr. B 1972, 28, 2659 (toluoyl chlorides). Le Carpentier, J.-M.; Weiss, R. Acta Crystallogr. B 1972, 28, 1437 (propionyl chloride).
14. 3, see: Rasmussen, S. E.; Broch, N. C. Acta Chem. Scand. 1966, 20, 1351 (benzoyl chloride). Chevrier, P. B.; Le Carpentier, J.-M.; Weiss, R. Acta Crystallogr. B 1972, 28, 2659 (toluoyl chlorides). Le Carpentier, J.-M.; Weiss, R. Acta Crystallogr. B 1972, 28, 1437 (propionyl chloride).
15. Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.