Reactivity and Diastereoselectivity in the Thermal and Lewis Acid-Catalyzed Diels-Alder Reactions of N-Sulfinylphosphoramidates

Journal of Organic Chemistry

Volumn 63, Issue 5, 1998, Pages 1372-1378

  Zhang, Yinsheng ^a,b   Flann, Christopher J ^a,c  

^a UNIVERSITY OF MONTANA   (United States)

^b Le Research Inc   (United States)

^c Moulton Bellingham Longo M   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKADIENE; IMIDAZOLE DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032489336     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970186t     Document Type: Article

References (31)

1. Presented at the 47th Northwest Regional Meeting of ACS, Missoula, MT, 1992, ORGN 116.
2. Wieczorkowski, J. Chem. Ind. 1963, 825.
3. Kataev, E. G.; Plemenkov, V. V.; Markin, V. V. Dokl. Akad. Nauk. SSSR 1965, 165, 1313.
4. Levchenko, E. S.; Bal'on, Ya G.; Kirsanov, A. V. Zk. Org. Khim. 1967, 30, 1883.
5. These reactions have been widely investigated from a synthetic and mechanistic perspective. For comprehensive reviews see: (a) Weinreb, S. M. Acc. Chem. Res. 1988, 21, 313. (b) Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Academic: San Diego, 1987; p 1. Bussas, P.; Kresze, G.; Munsterer, H.; Schwobel, A. Sulf. Rep. 1983, 2, 215.
6. These reactions have been widely investigated from a synthetic and mechanistic perspective. For comprehensive reviews see: (a) Weinreb, S. M. Acc. Chem. Res. 1988, 21, 313. (b) Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Academic: San Diego, 1987; p 1. Bussas, P.; Kresze, G.; Munsterer, H.; Schwobel, A. Sulf. Rep. 1983, 2, 215.
7. These reactions have been widely investigated from a synthetic and mechanistic perspective. For comprehensive reviews see: (a) Weinreb, S. M. Acc. Chem. Res. 1988, 21, 313. (b) Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Academic: San Diego, 1987; p 1. Bussas, P.; Kresze, G.; Munsterer, H.; Schwobel, A. Sulf. Rep. 1983, 2, 215.
8. Flann, C. J. Book of Abstracts; ACS 32nd National Organic Chemistry Symposium, American Chemical Society: Washington, DC, 1991, p 288.
9. Atherton, F. R.; Openshaw, T. H.; Todd, A. R. J. Org. Chem. 1945, 663.
10. Kim, Y. H.; Shin, J. M. Tetrahedron Lett. 1985, 26, 3821.
11. (a) Kashman, Y.; Awerbough, O. Tetrahedron 1971, 5593.
12. (b) Pankiewicz, Z.; Kinas, R.; Stec, W. J. J. Am. Chem. Soc. 1979, 101, 7712.
13. Cerioni, G.; Piras, P. J. Chem. Soc., Perkin Trans. 2 1981, 1449.
14. 13C NMR of carbonyl compounds have been investigated. Our results were consistent with Previous reports cited above.
15. We could not characterize compounds formed in the cycloaddition since they were extremely unstable.
16. Natsugari, H.; Whittle, R. R.; Weinreb, S. M. J. Am. Chem. Soc. 1984, 106, 7867.
17. Mock, W. L.; Nugent, R. M. J. Am. Chem. Soc. 1975, 97, 6521.
18. Garigipati, R. S.; Cordova, R.; Parvez, M.; Weinreb, S. M. Tetrahedron 1986, 42, 2979.
19. (a) Garigipati R. S.; Freyer, A. J.; Whittle, R. R.; Weinreb, S. M. J. Am. Chem. Soc. 1984, 106, 7861.
20. (b) Bell, S. I.; Parvez, M.; Weinreb, S. M. J. Org. Chem. 1991, 56, 373.
21. The author has deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2, 1EZ, UK.
22. 13C NMR of known endo sulfur epimers 7a,b,c. The structure details of these compounds will be published elsewhere.
23. Remiszewski, S. W.; Yang, J.; Weinreb, S. M. Tetrahedron Lett. 1986, 27, 1853.
24. Whitesell, J. K.; James, D.; Carpenter, J. F. J. Chem. Soc., Chem. Commun. 1985, 1449. In Whitesell's proposal, the transition states are labeled exo or endo with respect to the carbamate group. In our application of these possible transition states 17-20 endo refers to the sulfinyl group.
25. (a) Castellino, S. J. Org. Chem. 1990, 55, 5197 and also see references cited there.
26. 119Sn NMR Parameters; Academic Press: London, 1985; p 73.
27. (a) Bodalski, R.; Koszak, J.; Krawczyk, H.; Pietrusiewicz, K. M. J. Org. Chem. 1982, 47, 2219.
28. (b) Daniewski, W. M.; Griffin, C. E. J. Org. Chem. 1966, 31, 3236.
29. Zwierzak, A.; Koziara, A. Tetrahedron 1970, 26, 3521.
30. (a) Israili, Z. H.; Perel, J. M. J. Med. Chem. 1972, 15, 709.
31. (b) Deyrup, J. A.; Moyer, C. L. J. Org. Chem. 1969, 34, 175.