A silicon tether approach for diastereocontrol in radical addition to chiral hydrazones

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1499-1501

  Friestad, Gregory K ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000657404     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991059h     Document Type: Article

References (56)

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2. Reviews of methods for amino alcohol synthesis: Reets, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. For ionic C-C bond construction approaches, see: Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61 2677. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
3. Reviews of methods for amino alcohol synthesis: Reets, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. For ionic C-C bond construction approaches, see: Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61 2677. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
4. Reviews of methods for amino alcohol synthesis: Reets, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. For ionic C-C bond construction approaches, see: Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61 2677. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
5. Reviews of methods for amino alcohol synthesis: Reets, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. For ionic C-C bond construction approaches, see: Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61 2677. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
6. Reviews of methods for amino alcohol synthesis: Reets, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. For ionic C-C bond construction approaches, see: Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61 2677. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
7. Reviews of methods for amino alcohol synthesis: Reets, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. For ionic C-C bond construction approaches, see: Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61 2677. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
8. Recent examples in natural product synthesis: Boger, D. L.; Ledeboer, M. W.; Kume, M. J. Am. Chem. Soc. 1999, 121, 1098. Ghosh, A. K.; Wang, Y. J. Org. Chem. 1999, 64, 2789. Deng, J.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627.
9. Recent examples in natural product synthesis: Boger, D. L.; Ledeboer, M. W.; Kume, M. J. Am. Chem. Soc. 1999, 121, 1098. Ghosh, A. K.; Wang, Y. J. Org. Chem. 1999, 64, 2789. Deng, J.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627.
10. Recent examples in natural product synthesis: Boger, D. L.; Ledeboer, M. W.; Kume, M. J. Am. Chem. Soc. 1999, 121, 1098. Ghosh, A. K.; Wang, Y. J. Org. Chem. 1999, 64, 2789. Deng, J.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627.
11. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portunovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138.
12. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portunovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138.
13. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portunovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138.
14. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portunovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138.
15. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portunovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138.
16. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portunovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138.
17. Even organocerium reagents, considered relatively nonbasic nucleophiles, can promote aza-enolization of hydrazones. Enders, D.; Diez, E.; Fernandez, R.; Martin-Zamora, E.; Munoz, J. M.; Pappalardo, R. R.; Lassaleta, J. M. J. Org. Chem. 1999, 64, 6329.
18. Mild, stereoselective additions to aldehyde imino derivatives are a prominent current challenge. For notable efforts and leading references, see: Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450.
19. Mild, stereoselective additions to aldehyde imino derivatives are a prominent current challenge. For notable efforts and leading references, see: Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450.
20. Mild, stereoselective additions to aldehyde imino derivatives are a prominent current challenge. For notable efforts and leading references, see: Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450.
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25. (c) General reviews of radical reactions in organic synthesis: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds: Pergamon Press: New York, 1986. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
26. Only two studies showing acyclic stereocontrol in radical addition to C=N acceptors have appeared to date: Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789. Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780. For acyclic stereocontrol in radical addition to C=C bonds, see: Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163 and references therein.
27. Only two studies showing acyclic stereocontrol in radical addition to C=N acceptors have appeared to date: Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789. Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780. For acyclic stereocontrol in radical addition to C=C bonds, see: Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163 and references therein.
28. Only two studies showing acyclic stereocontrol in radical addition to C=N acceptors have appeared to date: Miyabe, H.; Ushiro, C.; Naito, T. J. Chem. Soc., Chem. Commun. 1997, 1789. Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780. For acyclic stereocontrol in radical addition to C=C bonds, see: Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163 and references therein.
29. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: New York; 1995.
30. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. Reviews: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. For a recent nonradical application to amino alcohol synthesis, see: Righi, P.; Marotta, E.; Rosini, G. Chem. Eur. J. 1998, 4, 2501.
31. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. Reviews: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. For a recent nonradical application to amino alcohol synthesis, see: Righi, P.; Marotta, E.; Rosini, G. Chem. Eur. J. 1998, 4, 2501.
32. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. Reviews: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. For a recent nonradical application to amino alcohol synthesis, see: Righi, P.; Marotta, E.; Rosini, G. Chem. Eur. J. 1998, 4, 2501.
33. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. Reviews: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. For a recent nonradical application to amino alcohol synthesis, see: Righi, P.; Marotta, E.; Rosini, G. Chem. Eur. J. 1998, 4, 2501.
34. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. Reviews: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. For a recent nonradical application to amino alcohol synthesis, see: Righi, P.; Marotta, E.; Rosini, G. Chem. Eur. J. 1998, 4, 2501.
35. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. Reviews: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253. For a recent nonradical application to amino alcohol synthesis, see: Righi, P.; Marotta, E.; Rosini, G. Chem. Eur. J. 1998, 4, 2501.
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37. Importantly, the silicon tether should permit introduction of a variety of functionalized fragments in addition to hydroxymethyl. Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984.
38. Esters 1 are prepared easily by standard methods from commercially available hydroxy acids or amino acids.
39. 13C NMR, IR, MS), and optical rotation. See Supporting Information.
40. Hydrazones 2-4 were essentially single isomers (>98:2) with respect to the C=N bond; only 2a-4a contained detectable traces (<5%) of a minor isomer. Aldehyde hydrazones are generally obtained as E isomers. Enders, D. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; pp 275-339.
41. Cyclization substrates 4 were purified rapidly by flash chromatography and used immediately in the next step.
42. Mosher ester analysis confirmed that the integrity of the preexisting stereocenter was maintained through the sequence to diols 6b and 6c (>96% ee). However, alcohol 3d, wherein the phenyl group can promote enolization. suffered significant racemization en route to 6d. The α-hydroxy and α-silyloxy hydrazones without additional carbanion-stabilizing functionality are configurationally stable under these conditions.
43. Tamao, K.; Ishida, N.; Ito, Y.; Kumada, M. Organic Syntheses; Wiley: New York, 1993; Collect. Vol. 8, p 315.
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46. Mori, K.; Uenishi, K. Liebigs Ann. Chem. 1994, 41. Barrett, A. G. M.; Rys, D. J. Chem. Soc., Perkin Trans. 1 1995, 1009. Han, B. H.; Kim, J. C.; Park, M. K.; Park, J. H.; Go, H. J.; Yang, H. D.; Suh, D.-Y.; Kang, Y.-H. Heterocycles 1995, 41, 1909. Herold, P. Helv. Chim. Acta 1988, 71, 354.
47. Mori, K.; Uenishi, K. Liebigs Ann. Chem. 1994, 41. Barrett, A. G. M.; Rys, D. J. Chem. Soc., Perkin Trans. 1 1995, 1009. Han, B. H.; Kim, J. C.; Park, M. K.; Park, J. H.; Go, H. J.; Yang, H. D.; Suh, D.-Y.; Kang, Y.-H. Heterocycles 1995, 41, 1909. Herold, P. Helv. Chim. Acta 1988, 71, 354.
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52. Cyclohexane terminology for 5-hexenyl radical transition states is the current convention. See ref 8 for discussion.
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