Face-selectivity in [4+2]-cycloadditions to novel polycyclic benzoquinones. Remarkable stereodirecting effects of a remote cyclopropane ring and an olefinic bond

Tetrahedron Letters

Volumn 44, Issue 15, 2003, Pages 3109-3113

  Mehta, Goverdhan ^a   Le Droumaguet, Celine ^a   Islam, Kabirul ^a   Anoop, Anakuthil ^b   Jemmis, Eluvathingal D ^b  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BENZOQUINONE DERIVATIVE; CYCLOPROPANE;

ARTICLE; CHEMICAL BOND; CYCLOADDITION; DIELS ALDER REACTION; QUANTUM MECHANICS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0037424780     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00504-5     Document Type: Article

References (30)

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5. Selected references: (a) Angell, E. C.; Fringuelli, F.; Pizzo, P.; Tatichhi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642; (b) Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050; (c) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663; (d) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136; (e) Fessner, W. D.; Grund, C.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5935; (f) Mehta, G.; Padma, S.; Reddy, H. K.; Nethaji, M. J. Chem. Soc., Perkin Trans. 1 1994, 2049; (g) Mehta, G.; Uma, R. Tetrahedron Lett. 1995, 36, 4873; (h) Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939; (i) Mehta, G.; Uma, R. J. Org. Chem. 2000, 65, 1685.
6. Selected references: (a) Angell, E. C.; Fringuelli, F.; Pizzo, P.; Tatichhi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642; (b) Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050; (c) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663; (d) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136; (e) Fessner, W. D.; Grund, C.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5935; (f) Mehta, G.; Padma, S.; Reddy, H. K.; Nethaji, M. J. Chem. Soc., Perkin Trans. 1 1994, 2049; (g) Mehta, G.; Uma, R. Tetrahedron Lett. 1995, 36, 4873; (h) Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939; (i) Mehta, G.; Uma, R. J. Org. Chem. 2000, 65, 1685.
7. Selected references: (a) Angell, E. C.; Fringuelli, F.; Pizzo, P.; Tatichhi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642; (b) Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050; (c) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663; (d) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136; (e) Fessner, W. D.; Grund, C.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5935; (f) Mehta, G.; Padma, S.; Reddy, H. K.; Nethaji, M. J. Chem. Soc., Perkin Trans. 1 1994, 2049; (g) Mehta, G.; Uma, R. Tetrahedron Lett. 1995, 36, 4873; (h) Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939; (i) Mehta, G.; Uma, R. J. Org. Chem. 2000, 65, 1685.
8. Selected references: (a) Angell, E. C.; Fringuelli, F.; Pizzo, P.; Tatichhi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642; (b) Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050; (c) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663; (d) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136; (e) Fessner, W. D.; Grund, C.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5935; (f) Mehta, G.; Padma, S.; Reddy, H. K.; Nethaji, M. J. Chem. Soc., Perkin Trans. 1 1994, 2049; (g) Mehta, G.; Uma, R. Tetrahedron Lett. 1995, 36, 4873; (h) Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939; (i) Mehta, G.; Uma, R. J. Org. Chem. 2000, 65, 1685.
9. Selected references: (a) Angell, E. C.; Fringuelli, F.; Pizzo, P.; Tatichhi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642; (b) Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050; (c) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663; (d) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136; (e) Fessner, W. D.; Grund, C.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5935; (f) Mehta, G.; Padma, S.; Reddy, H. K.; Nethaji, M. J. Chem. Soc., Perkin Trans. 1 1994, 2049; (g) Mehta, G.; Uma, R. Tetrahedron Lett. 1995, 36, 4873; (h) Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939; (i) Mehta, G.; Uma, R. J. Org. Chem. 2000, 65, 1685.
10. Selected references: (a) Angell, E. C.; Fringuelli, F.; Pizzo, P.; Tatichhi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642; (b) Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050; (c) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663; (d) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136; (e) Fessner, W. D.; Grund, C.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5935; (f) Mehta, G.; Padma, S.; Reddy, H. K.; Nethaji, M. J. Chem. Soc., Perkin Trans. 1 1994, 2049; (g) Mehta, G.; Uma, R. Tetrahedron Lett. 1995, 36, 4873; (h) Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939; (i) Mehta, G.; Uma, R. J. Org. Chem. 2000, 65, 1685.
11. Selected references: (a) Angell, E. C.; Fringuelli, F.; Pizzo, P.; Tatichhi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642; (b) Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050; (c) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663; (d) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136; (e) Fessner, W. D.; Grund, C.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5935; (f) Mehta, G.; Padma, S.; Reddy, H. K.; Nethaji, M. J. Chem. Soc., Perkin Trans. 1 1994, 2049; (g) Mehta, G.; Uma, R. Tetrahedron Lett. 1995, 36, 4873; (h) Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939; (i) Mehta, G.; Uma, R. J. Org. Chem. 2000, 65, 1685.
12. Selected references: (a) Angell, E. C.; Fringuelli, F.; Pizzo, P.; Tatichhi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642; (b) Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050; (c) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663; (d) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136; (e) Fessner, W. D.; Grund, C.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5935; (f) Mehta, G.; Padma, S.; Reddy, H. K.; Nethaji, M. J. Chem. Soc., Perkin Trans. 1 1994, 2049; (g) Mehta, G.; Uma, R. Tetrahedron Lett. 1995, 36, 4873; (h) Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939; (i) Mehta, G.; Uma, R. J. Org. Chem. 2000, 65, 1685.
13. Selected references: (a) Angell, E. C.; Fringuelli, F.; Pizzo, P.; Tatichhi, A.; Wenkert, E. J. Org. Chem. 1986, 51, 2642; (b) Brown, F. K.; Houk, K. N.; Burnell, D. J.; Valenta, Z. J. Org. Chem. 1987, 52, 3050; (c) Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663; (d) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136; (e) Fessner, W. D.; Grund, C.; Prinzbach, H. Tetrahedron Lett. 1991, 32, 5935; (f) Mehta, G.; Padma, S.; Reddy, H. K.; Nethaji, M. J. Chem. Soc., Perkin Trans. 1 1994, 2049; (g) Mehta, G.; Uma, R. Tetrahedron Lett. 1995, 36, 4873; (h) Wellman, M. A.; Burry, L. C.; Letourneau, J. E.; Bridson, J. N.; Miller, D. O.; Burnell, D. J. J. Org. Chem. 1997, 62, 939; (i) Mehta, G.; Uma, R. J. Org. Chem. 2000, 65, 1685.
14. Reviews: (a) Ohwada, T. Chem. Rev. 1999, 99, 1337; (b) Coxon, J. M.; Froese, R. D. G.; Ganguli, B.; Marchand, A. Synlett 1999, 1681; (c) Mehta, G.; Uma, R. Acc. Chem. Res. 2000, 33, 278; (d) Marchand, A., Coxon, J. M. Acc. Chem. Res. 2002, 35, 271.
15. Reviews: (a) Ohwada, T. Chem. Rev. 1999, 99, 1337; (b) Coxon, J. M.; Froese, R. D. G.; Ganguli, B.; Marchand, A. Synlett 1999, 1681; (c) Mehta, G.; Uma, R. Acc. Chem. Res. 2000, 33, 278; (d) Marchand, A., Coxon, J. M. Acc. Chem. Res. 2002, 35, 271.
16. Reviews: (a) Ohwada, T. Chem. Rev. 1999, 99, 1337; (b) Coxon, J. M.; Froese, R. D. G.; Ganguli, B.; Marchand, A. Synlett 1999, 1681; (c) Mehta, G.; Uma, R. Acc. Chem. Res. 2000, 33, 278; (d) Marchand, A., Coxon, J. M. Acc. Chem. Res. 2002, 35, 271.
17. Reviews: (a) Ohwada, T. Chem. Rev. 1999, 99, 1337; (b) Coxon, J. M.; Froese, R. D. G.; Ganguli, B.; Marchand, A. Synlett 1999, 1681; (c) Mehta, G.; Uma, R. Acc. Chem. Res. 2000, 33, 278; (d) Marchand, A., Coxon, J. M. Acc. Chem. Res. 2002, 35, 271.
18. Edman J.R., Simmons H.E. J. Org. Chem. 33:1968;3808.
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20. Mehta G., Reddy H.K., Reddy D.S.K. Tetrahedron Lett. 32:1991;6399.
21. Mehta G., Reddy H.K. Angew. Chem. Int. Ed. 32:1993;1160.
22. Carreno M. Chem. Rev. 95:1995;1717.
23. Okamoto I., Ohwada T., Schdo K. J. Org. Chem. 61:1996;3155.
24. Bicyclo[2.2.2]annulated benzoquinones 4-8 were prepared from the Diels-Alder adducts of benzoquinone with 1,3-cyclohexadiene, 1,3,5-cycloheptatriene and cyclooctatetraene, respectively, and further transformations patterned along the procedure described in: (a) Cookson, R. C.; Hill, R. R.; Hudec, J. J. Chem. Soc. 1964, 3043; (b) Mehta, G.; Padma, S. J. Am. Chem. Soc. 1987, 109, 7230. Details of the syntheses of 4-8 will be described in the full paper.
25. Bicyclo[2.2.2]annulated benzoquinones 4-8 were prepared from the Diels-Alder adducts of benzoquinone with 1,3-cyclohexadiene, 1,3,5-cycloheptatriene and cyclooctatetraene, respectively, and further transformations patterned along the procedure described in: (a) Cookson, R. C.; Hill, R. R.; Hudec, J. J. Chem. Soc. 1964, 3043; (b) Mehta, G.; Padma, S. J. Am. Chem. Soc. 1987, 109, 7230. Details of the syntheses of 4-8 will be described in the full paper.
26. The X-ray crystal data for annulated quinones 5 and 7 will be reported elsewhere.
27. 2).
28. o) and 0.1237 for all 2237 data. GOF=1.198, Restrained GOF=1.198 for all data, CCDC 203636. ORTEP drawings of compounds 10, 13, 22 and 26 with 50% ellipsoidal probability are shown below.
29. Hoffmann R., Davidson R.B. J. Am. Chem. Soc. 93:1971;5699.
30. Frisch M.J., Trucks G.W., Schelegel H.B., Gill P.M.W., Johnson B.G., Robb M.A., Cheeseman J.R., Keith T., Peterson G.A., Montgomery J.A., Raghavachari K., Al-Laham M.A., Zakrzewski V.G., Ortiz J.V., Foresman J.B., Cioslowsky J., Stefenov B.B., Nanayakkara A., Challacombe M., Peng C.Y., Ayala P.Y., Chen W., Wong M.W., Andres J.L., Replogle E.S., Gomberts R., Martin R.L., Fox D.J., Binkley J.S., Defrees D.J., Baker J., Stewart J.P., Head-Gordon M., Gonzalez C., Pople J.A. Gaussian 94, Revision D.1. 1995;Gaussian, Inc, Pittsburg, PA.