Lewis Acid-Promoted Reactions of 3-Methoxy-N-(benzenesulfonyl)-1,4-benzoquinone Monoimine with Propenylbenzenes

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6247-6253

  Engler, Thomas A ^a,b   Scheibe, Cynthia M ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542397191     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980502j     Document Type: Article

References (20)

1. (a) Engler, T. A.; Combrink, K. D.; Letavic, M. A.; Lynch, K. O., Jr.; Ray, J. E. J. Org. Chem. 1994, 59, 6567-6587.
2. (b) Engler, T. A.; Wei, D.; Letavic, M. A.; Combrink, K. D.; Reddy, J. P. J. Org. Chem. 1994, 59, 6588-6599.
3. Engler, T. A.; Meduna, S. P.; LaTessa, K. O.; Chai, W. J. Org. Chem. 1996, 61, 8598-8603.
4. Engler, T. A.; Chai, W.; LaTessa, K. O. J. Org. Chem. 1996, 61, 9297-9308.
5. (a) Boger, D. L.; Zarrinmayeh, H. J. Org. Chem. 1990, 55, 1379-1390.
6. (b) Boger, D. L.; Coleman, R. S. J. Am. Chem. Soc. 1988, 110, 4796-4807.
7. Adams, R.; Reifschneider, W. Bull. Chim. Soc. Fr. 1958, 23-65.
8. Monoimine 5 was prepared in two steps from 2,4-dimethoxyaniline.
9. Swenton has demonstrated that N-acyl-1,4-benzoquinone imines play a role in acid-catalyzed reactions of N-acylquinone imine ketals with propenylbenzenes that give dihydrobenzofurans and dihydroindoles, Dalidowicz, P.; Swenton, J. S.V. Org. Chem. 1993, 58, 4802-4804.
10. X-ray data and summaries of NOE data can be found in the Supporting Information accompanying our preliminary report: Engler, T. A.; Scheibe, C. M.; Iyengar, R. J. Org. Chem. 1997, 62, 8274-8275.
11. The presence of unidentified minor peaks in the HPLC traces complicated an accurate determination of product ratios; the ratios presented are approximate.
12. (a) Neighboring group participation via nitrogen of a sulfonamido group has been observed in reactions of 2-β-iodo-1-α-sulfonamidohexoses, Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 5811-5819.
13. - is perhaps possible; such interactions are found in the solid state, Laube, T. In Stable Carbocation Chemistry; Prakash, G. K. S., Schleyer, P.v. R., Eds.; Wiley: New York, 1997; Chp. 14.
14. (c) Participation via nitrogen is not geometrically feasible in 19, but participation through the sulfonyl group is worthy of consideration.
15. Engler, T. A.; Chai, W. Tetrahedron Lett. 1996, 37, 6969-6970.
16. (a) Engler, T. A.; Lynch, K. O., Jr.; Reddy, J. P.; Gregory, G. S. Bioorg. Med. Chem. Lett. 1993, 3, 1229-1232.
17. (b) Engler, T. A.; Lynch, K. O., Jr.; Iyengar, R.; Chai, W.; Agrios, K. Bioorg. Med. Chem. 1996, 4, 1755-1769.
18. (c) Engler, T. A.; Reddy, J. P.; Combrink, K. D.; Vander Velde, D. J. Org. Chem. 1990, 55, 1248-1254, and references therein.
19. (a) For a description of general experimental details, see Engler, T. A.; Luterman, D. R. J. Org. Chem. 1998, 63, 314-318.
20. (b) The propenylbenzenes employed were mixtures of (E):(Z) isomers (> 5:1) as described in refs 1-3 and 8a.