Designed Chiral Acyl Radical Equivalents. Preparation and Cyclizations of Disymmetrically Substituted 1,3-Dioxabicyclo[4.4.0]decan-2-yl Radicals

Journal of Organic Chemistry

Volumn 62, Issue 2, 1997, Pages 275-286

  Stien, D ^a,b   Samy, R ^b   Nouguier, R ^b   Crich, D ^b   Bertrand, M P ^a  

^a CNRS   (France)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000696586     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961750n     Document Type: Article

References (84)

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22. For reviews see: (c) Nájera, C.; Yus, M. Org. Prep. Proc. Int. 1995, 27, 383. (d) Crich, D.; Yuan, H. in Advances in Free Radical Chemistry; Rawal, V. K., Ed.; JAI: Greenwich, 1997; Vol. 2, in press.
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45. Lead references: (a) Crich, D.; Ritchie, T. J. Tetrahedron 1988, 44, 2319. (b) Crich, D.; Hermann, F. Tetrahedron Lett. 1993, 34, 3385. (c) Crich, D.; Sun, S.; Brunckova, J. J. Org. Chem. 1996, 61, 605. (d) Yamazaki, N.; Eichenberger, E. Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (e) Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am. Chem. Soc. 1988, 110, 8716. (f) Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 413.
46. Lead references: (a) Crich, D.; Ritchie, T. J. Tetrahedron 1988, 44, 2319. (b) Crich, D.; Hermann, F. Tetrahedron Lett. 1993, 34, 3385. (c) Crich, D.; Sun, S.; Brunckova, J. J. Org. Chem. 1996, 61, 605. (d) Yamazaki, N.; Eichenberger, E. Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (e) Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am. Chem. Soc. 1988, 110, 8716. (f) Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 413.
47. Lead references: (a) Crich, D.; Ritchie, T. J. Tetrahedron 1988, 44, 2319. (b) Crich, D.; Hermann, F. Tetrahedron Lett. 1993, 34, 3385. (c) Crich, D.; Sun, S.; Brunckova, J. J. Org. Chem. 1996, 61, 605. (d) Yamazaki, N.; Eichenberger, E. Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (e) Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am. Chem. Soc. 1988, 110, 8716. (f) Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 413.
48. Lead references: (a) Crich, D.; Ritchie, T. J. Tetrahedron 1988, 44, 2319. (b) Crich, D.; Hermann, F. Tetrahedron Lett. 1993, 34, 3385. (c) Crich, D.; Sun, S.; Brunckova, J. J. Org. Chem. 1996, 61, 605. (d) Yamazaki, N.; Eichenberger, E. Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (e) Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am. Chem. Soc. 1988, 110, 8716. (f) Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 413.
49. Lead references: (a) Crich, D.; Ritchie, T. J. Tetrahedron 1988, 44, 2319. (b) Crich, D.; Hermann, F. Tetrahedron Lett. 1993, 34, 3385. (c) Crich, D.; Sun, S.; Brunckova, J. J. Org. Chem. 1996, 61, 605. (d) Yamazaki, N.; Eichenberger, E. Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (e) Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am. Chem. Soc. 1988, 110, 8716. (f) Sugai, T.; Shen, G.-J.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 413.
50. 3CN; see: Kreevoy, M. M.; Hutchins, J. E. C. J. Am. Chem. Soc. 1969, 91, 4329.
51. (b) Two broad singlets were registered in the 2D spectrum at 3.69 and 0.98 ppm, respectively (4:1 relative integration).
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56. For examples of selective axial trapping of closely related radicals see: (a) Rychnovsky, S. D.; Skalitzky, D. J. Synlett 1995, 555. (b) Rychnovsky, S. D.; Plzak, K.; Pickering, D. Tetrahedron Lett. 1994, 35, 6799. (c) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969.
57. For examples of selective axial trapping of closely related radicals see: (a) Rychnovsky, S. D.; Skalitzky, D. J. Synlett 1995, 555. (b) Rychnovsky, S. D.; Plzak, K.; Pickering, D. Tetrahedron Lett. 1994, 35, 6799. (c) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969.
58. For the use of primary isotope effects to retard 1,5- and even intermolecular hydrogen atom abstractions see: (a) Clive, D. L. J.; Cantin, M.; Khodabocus, A.; Kong, X.; Tao, Y. Tetrahedron 1993, 49, 7917. (b) Warth, J. L.; Frank, B. L.; Christner, D. F.; Absalon, M. J.; Stubbe, J.; Kozarich, J. W. Biochemistry 1993, 32, 2601. (c) Sugiyama, H.; Fujimoto, K.; Saito, I.; Kawashima, E.; Sekine, T.; Ishido, Y. Tetrahedron Lett. 1996, 37, 1805.
59. For the use of primary isotope effects to retard 1,5- and even intermolecular hydrogen atom abstractions see: (a) Clive, D. L. J.; Cantin, M.; Khodabocus, A.; Kong, X.; Tao, Y. Tetrahedron 1993, 49, 7917. (b) Warth, J. L.; Frank, B. L.; Christner, D. F.; Absalon, M. J.; Stubbe, J.; Kozarich, J. W. Biochemistry 1993, 32, 2601. (c) Sugiyama, H.; Fujimoto, K.; Saito, I.; Kawashima, E.; Sekine, T.; Ishido, Y. Tetrahedron Lett. 1996, 37, 1805.
60. For the use of primary isotope effects to retard 1,5- and even intermolecular hydrogen atom abstractions see: (a) Clive, D. L. J.; Cantin, M.; Khodabocus, A.; Kong, X.; Tao, Y. Tetrahedron 1993, 49, 7917. (b) Warth, J. L.; Frank, B. L.; Christner, D. F.; Absalon, M. J.; Stubbe, J.; Kozarich, J. W. Biochemistry 1993, 32, 2601. (c) Sugiyama, H.; Fujimoto, K.; Saito, I.; Kawashima, E.; Sekine, T.; Ishido, Y. Tetrahedron Lett. 1996, 37, 1805.
61. For a compilation of ESR spectroscopic data for vinyl radicals see: Neugebauer, F. A. in Lanholt-Bornstein New Series; Fischer, H., Ed.; Springer-Verlag: Berlin, 1989; Vol. 17b, p 492. Also see: Simamura, O. Top. Stereochem. 1969, 4, 1.
62. For a compilation of ESR spectroscopic data for vinyl radicals see: Neugebauer, F. A. in Lanholt-Bornstein New Series; Fischer, H., Ed.; Springer-Verlag: Berlin, 1989; Vol. 17b, p 492. Also see: Simamura, O. Top. Stereochem. 1969, 4, 1.
63. A kinetically equivalent scheme applies to more conjugated π-type vinyl radicals such as the α-phenylvinyl system, which adopts a linear geometry with the single electron in an sp-hybrid (π-like) orbital with maximum stabilization from overlap with the conjugated moiety. Stereoselectivity is again determined by steric factors at the transition state for quenching.
64. In principle, this question may be addressed through the use of higher stannane concentrations such that, following 1,5-hydrogen atom abstraction, the dioxanyl radical is trapped by the stannane rather than by cyclization. In practice, such an approach is likely to result simply in the quenching of the vinyl radical by the stannane. Such experiments were therefore not attempted.
65. For substrates 11a,b, 14, 21, 39, and 45 there is also the possibility that, due to benzylic stabilization of the cyclized radicals rendering the cyclization more exothermic, the earlier transition state with its longer developing bond results in a reduction in energy differential between chairs F and G. We thank Professor P. J. Garner, Case Western Reserve University, for this insight; see ref 2b,c.
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67. trans-4,6-Disubstituted-2,2-dimethyl-l,3-dioxanes adopt twist- boat conformations: (a) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. (b) Rychnovsky, S. D.; Yang, G.; Powers, J. P. J. Org. Chem. 1993, 58, 5251. (c) For conformational analysis of 1,3- dioxanes: Antenuis, M. J. O.; Tavernier, D.; Borremans, F. Heterocycles 1976, 4, 293.
68. trans-4,6-Disubstituted-2,2-dimethyl-l,3-dioxanes adopt twist- boat conformations: (a) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. (b) Rychnovsky, S. D.; Yang, G.; Powers, J. P. J. Org. Chem. 1993, 58, 5251. (c) For conformational analysis of 1,3- dioxanes: Antenuis, M. J. O.; Tavernier, D.; Borremans, F. Heterocycles 1976, 4, 293.
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