C(10)-substituted camphors and fenchones by electrophilic treatment of 2-methylenenorbornan-1-ols: Enantiospecificity, scope, and limitations

Journal of Organic Chemistry

Volumn 68, Issue 4, 2003, Pages 1451-1458

  De la Moya Cerero, Santiago ^a   Martínez, Antonio García ^a   Vilar, Enrique Teso ^b   Fraile, Amelia García ^b   Maroto, Beatriz Lora ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

ELECTROPHILIC TREATMENT;

AROMATIC COMPOUNDS;

CAMPHOR DERIVATIVE; HYDROXYL GROUP; KETONE DERIVATIVE; NORBORNANE DERIVATIVE; 1,3,3 TRIMETHYL 2 NORCAMPHANONE; CAMPHOR; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HALOGENATED HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; SEPARATION TECHNIQUE; WAGNER MEERWEIN REARRANGEMENT; CATALYSIS; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CAMPHOR; CATALYSIS; CHEMISTRY, ORGANIC; HYDROCARBONS, HALOGENATED; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NORBORNANES; STEREOISOMERISM;

EID: 0242515867     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026566i     Document Type: Article

References (100)

1. Some interesting general reviews are: (a) Oppolzer, W. Tetrahedron 1987, 43, 1969. (b) Money, T. Nat. Prod. Rep. 1985, 2, 253. (c) Ho, T.-L. In Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley and Sons: New York. 1992. (d) Money, T. In Studies in Natural Products Chemistry; Atta-ur-Rahmann, Ed.; Elsevier: Amsterdam, The Netherlands, 1989. (e) Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; John Wiley and Sons: New York. 1994. (f) Seyden-Penne J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York. 1995.
2. Some interesting general reviews are: (a) Oppolzer, W. Tetrahedron 1987, 43, 1969. (b) Money, T. Nat. Prod. Rep. 1985, 2, 253. (c) Ho, T.-L. In Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley and Sons: New York. 1992. (d) Money, T. In Studies in Natural Products Chemistry; Atta-ur-Rahmann, Ed.; Elsevier: Amsterdam, The Netherlands, 1989. (e) Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; John Wiley and Sons: New York. 1994. (f) Seyden-Penne J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York. 1995.
3. Some interesting general reviews are: (a) Oppolzer, W. Tetrahedron 1987, 43, 1969. (b) Money, T. Nat. Prod. Rep. 1985, 2, 253. (c) Ho, T.-L. In Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley and Sons: New York. 1992. (d) Money, T. In Studies in Natural Products Chemistry; Atta-ur-Rahmann, Ed.; Elsevier: Amsterdam, The Netherlands, 1989. (e) Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; John Wiley and Sons: New York. 1994. (f) Seyden-Penne J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York. 1995.
4. Some interesting general reviews are: (a) Oppolzer, W. Tetrahedron 1987, 43, 1969. (b) Money, T. Nat. Prod. Rep. 1985, 2, 253. (c) Ho, T.-L. In Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley and Sons: New York. 1992. (d) Money, T. In Studies in Natural Products Chemistry; Atta-ur-Rahmann, Ed.; Elsevier: Amsterdam, The Netherlands, 1989. (e) Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; John Wiley and Sons: New York. 1994. (f) Seyden-Penne J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York. 1995.
5. Some interesting general reviews are: (a) Oppolzer, W. Tetrahedron 1987, 43, 1969. (b) Money, T. Nat. Prod. Rep. 1985, 2, 253. (c) Ho, T.-L. In Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley and Sons: New York. 1992. (d) Money, T. In Studies in Natural Products Chemistry; Atta-ur-Rahmann, Ed.; Elsevier: Amsterdam, The Netherlands, 1989. (e) Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; John Wiley and Sons: New York. 1994. (f) Seyden-Penne J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York. 1995.
6. Some interesting general reviews are: (a) Oppolzer, W. Tetrahedron 1987, 43, 1969. (b) Money, T. Nat. Prod. Rep. 1985, 2, 253. (c) Ho, T.-L. In Enantioselective Synthesis: Natural Products from Chiral Terpenes; John Wiley and Sons: New York. 1992. (d) Money, T. In Studies in Natural Products Chemistry; Atta-ur-Rahmann, Ed.; Elsevier: Amsterdam, The Netherlands, 1989. (e) Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; John Wiley and Sons: New York. 1994. (f) Seyden-Penne J. In Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York. 1995.
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8. Some recent examples are the following: concerning the C1/C2 fragmentation: (a) Mermet-Mouttet, M. P.; Gabriel, K.; Heissler, D. Tetrahedron Lett. 1999, 40, 843. (b) Mehta, G.; Mohal, N. Tetrahedron Lett. 1999, 40, 5791 and 5795. (c) Mehta, G.; Venkateswaran, R. V. Tetrahedron 2000, 56, 1399. (d) Mehta, G.; Mohal, N. Tetrahedron Lett. 2001, 42, 4227. Concerning the C2/C3 fragmentation see: (e) Nagakawa, H.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 4523. (f) Hoveyda, A. H.; Schrock, R. R. Chem. Eur. J. 2001, 7, 945. Also see refs 1b and 8.
9. Some recent examples are the following: concerning the C1/C2 fragmentation: (a) Mermet-Mouttet, M. P.; Gabriel, K.; Heissler, D. Tetrahedron Lett. 1999, 40, 843. (b) Mehta, G.; Mohal, N. Tetrahedron Lett. 1999, 40, 5791 and 5795. (c) Mehta, G.; Venkateswaran, R. V. Tetrahedron 2000, 56, 1399. (d) Mehta, G.; Mohal, N. Tetrahedron Lett. 2001, 42, 4227. Concerning the C2/C3 fragmentation see: (e) Nagakawa, H.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 4523. (f) Hoveyda, A. H.; Schrock, R. R. Chem. Eur. J. 2001, 7, 945. Also see refs 1b and 8.
10. Some recent examples are the following: concerning the C1/C2 fragmentation: (a) Mermet-Mouttet, M. P.; Gabriel, K.; Heissler, D. Tetrahedron Lett. 1999, 40, 843. (b) Mehta, G.; Mohal, N. Tetrahedron Lett. 1999, 40, 5791 and 5795. (c) Mehta, G.; Venkateswaran, R. V. Tetrahedron 2000, 56, 1399. (d) Mehta, G.; Mohal, N. Tetrahedron Lett. 2001, 42, 4227. Concerning the C2/C3 fragmentation see: (e) Nagakawa, H.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 4523. (f) Hoveyda, A. H.; Schrock, R. R. Chem. Eur. J. 2001, 7, 945. Also see refs 1b and 8.
11. Some recent examples are the following: concerning the C1/C2 fragmentation: (a) Mermet-Mouttet, M. P.; Gabriel, K.; Heissler, D. Tetrahedron Lett. 1999, 40, 843. (b) Mehta, G.; Mohal, N. Tetrahedron Lett. 1999, 40, 5791 and 5795. (c) Mehta, G.; Venkateswaran, R. V. Tetrahedron 2000, 56, 1399. (d) Mehta, G.; Mohal, N. Tetrahedron Lett. 2001, 42, 4227. Concerning the C2/C3 fragmentation see: (e) Nagakawa, H.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 4523. (f) Hoveyda, A. H.; Schrock, R. R. Chem. Eur. J. 2001, 7, 945. Also see refs 1b and 8.
12. Some recent examples are the following: concerning the C1/C2 fragmentation: (a) Mermet-Mouttet, M. P.; Gabriel, K.; Heissler, D. Tetrahedron Lett. 1999, 40, 843. (b) Mehta, G.; Mohal, N. Tetrahedron Lett. 1999, 40, 5791 and 5795. (c) Mehta, G.; Venkateswaran, R. V. Tetrahedron 2000, 56, 1399. (d) Mehta, G.; Mohal, N. Tetrahedron Lett. 2001, 42, 4227. Concerning the C2/C3 fragmentation see: (e) Nagakawa, H.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 4523. (f) Hoveyda, A. H.; Schrock, R. R. Chem. Eur. J. 2001, 7, 945. Also see refs 1b and 8.
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40. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
41. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
42. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
43. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
44. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
45. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
46. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
47. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
48. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
49. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
50. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
51. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
52. For example, see the following: Referred to C(10)-O- substituted camphors: (a) Chu, Y.-Y.; Yu, C.-S.; Chen, C.-J.; Yang, K.-S.; Lian, J.-C.; Lin, C.-H.; Chen, K. J. Org. Chem. 1999, 64, 6993. (b) Hiroi, K.; Watanabe, K. Tetrahedron: Asymmetry 2001, 12, 3067. Referred to C(10)-N-substituted camphors: (c) Seo, R.; Ishizuka, T.; Abdel-Aziz, A. A.-M.; Kunieda, T. Tetrahedron Lett. 2001, 42, 6353. (d) Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2001, 42, 4837. (e) Yang, K.-S.; Chen, K. J. Org. Chem. 2001, 66, 1676. Referred to C10-halogen -substituted camphors: (f) Fergurson, C. G.; Money, T.; Portillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron 1996, 52, 14461. Referred to C(10)P-substituted camphors: (g) Komarov, I. V.; Gorichko, M. V.; Kornilov, M. Tetrahedron: Asymmetry 1997, 8, 435. (h) Sell, T.; Laschat, S.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 4119. (i) Monsess, A.; Laschat, S. Synlett 2002, 1011. Referred to C(10)-Se-substituted camphors: (j) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (k) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1. Referred to C(10)-Te-substituted camphors: (l) Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 5423. Referred to C(10)C-substituted camphors, see refs 5 and 8.
53. For the influence of the topological differences of camphor- and fenchone-derived chiral sources on the chirality transfer, see: (a) Genov, M.; Kostova, K.; Dimitrov, V. Tetrahedron Asymmetry 1997, 8, 1869. (b) Suzuki, Y.; Ogata, Y.; Hiroi, K. Tetrahedron: Asymmetry 1999, 10, 1219. (c) Page, P. C. B.; Murrell, V. L.; Limousin, C.; Laffan, D. D. P.; Bethell, D.; Slawin, A. M. Z.; Smith, T. A. D. J. Org. Chem. 2000, 65, 4204. Also see refs 5 and 13g.
54. For the influence of the topological differences of camphor- and fenchone-derived chiral sources on the chirality transfer, see: (a) Genov, M.; Kostova, K.; Dimitrov, V. Tetrahedron Asymmetry 1997, 8, 1869. (b) Suzuki, Y.; Ogata, Y.; Hiroi, K. Tetrahedron: Asymmetry 1999, 10, 1219. (c) Page, P. C. B.; Murrell, V. L.; Limousin, C.; Laffan, D. D. P.; Bethell, D.; Slawin, A. M. Z.; Smith, T. A. D. J. Org. Chem. 2000, 65, 4204. Also see refs 5 and 13g.
55. For the influence of the topological differences of camphor- and fenchone-derived chiral sources on the chirality transfer, see: (a) Genov, M.; Kostova, K.; Dimitrov, V. Tetrahedron Asymmetry 1997, 8, 1869. (b) Suzuki, Y.; Ogata, Y.; Hiroi, K. Tetrahedron: Asymmetry 1999, 10, 1219. (c) Page, P. C. B.; Murrell, V. L.; Limousin, C.; Laffan, D. D. P.; Bethell, D.; Slawin, A. M. Z.; Smith, T. A. D. J. Org. Chem. 2000, 65, 4204. Also see refs 5 and 13g.
56. For the preparation of 10-fenchonesulfonic acid, see: Verfürth, V.; Ugi, I. Chem. Ber. 1991, 124, 1627.
57. (a) García Martínez, A.; Teso Vilar, E.; García Fraile, A.; de la Moya Cerero, S.; Díaz Oliva, C.; Subramanian, L. R.; Maichle, C. Tetrahedron: Asymmetry 1994, 5, 949.
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74. Forster, M. O. J. Chem. Soc. 1901, 79, 644.
75. D-40.2 in absolute ethanol.
76. (a) Eck, R.; Mills, R. W.; Money, T. J. Chem. Soc., Perkin Trans. 1 1975, 521.
77. (b) Money, T.; Palme, M. H. Tetrahedron: Asymmetry 1993, 4, 2363. Also see ref 13f.
78. This bridgehead-substituent effect has been previously demonstrated in: (a) Paukstelis, J. V.; Macharia, B. W. Chem. Commun. 1970, 131. Also see: (b) Thomas, A. A.; Monk, K. A.; Abraham, S.; Lee, S.; Garner, C. M. Tetrahedron Lett. 2001, 42, 2261. (c) Gosselin, P.; Lelièvre, M.; Poissonnier, B. Tetrahedron: Asymmetry 2001, 12, 2091.
79. This bridgehead-substituent effect has been previously demonstrated in: (a) Paukstelis, J. V.; Macharia, B. W. Chem. Commun. 1970, 131. Also see: (b) Thomas, A. A.; Monk, K. A.; Abraham, S.; Lee, S.; Garner, C. M. Tetrahedron Lett. 2001, 42, 2261. (c) Gosselin, P.; Lelièvre, M.; Poissonnier, B. Tetrahedron: Asymmetry 2001, 12, 2091.
80. This bridgehead-substituent effect has been previously demonstrated in: (a) Paukstelis, J. V.; Macharia, B. W. Chem. Commun. 1970, 131. Also see: (b) Thomas, A. A.; Monk, K. A.; Abraham, S.; Lee, S.; Garner, C. M. Tetrahedron Lett. 2001, 42, 2261. (c) Gosselin, P.; Lelièvre, M.; Poissonnier, B. Tetrahedron: Asymmetry 2001, 12, 2091.
81. Forster, M. O. J. Chem. Soc. 1902, 81, 264.
82. By the measurement of the specific optical rotation.
83. The bromine atom of 10a(Br) can be easily replaced by other functional groups via a nucleophilic-substitution reaction. As an example see: Dallacker, F.; Alroggen, I.; Krings, H.; Laurs, B.; Lipp. M. Liebigs Ann. Chem. 1961, 647, 23. Also see refs 10g, hj, l.
84. (a) Libman, J.; Sprecher, M.; Mazur, Y. Tetrahedron 1969, 25, 1679. Nonoptically pure 9a can be obtained in better yield through another synthetic route (see ref 18a and references therein).
85. C(8)-substituted camphor derivatives are spectroscopically quite different from the corresponding C(10)-substituted camphors. As an example, see the described spectroscopic data for 8-bromocamphor [15a(Br)] in ref 17a.
86. + see: (b) Masson, S.; Thuillier, A. Bull. Soc. Chim. Fr. 1969, 4368. (c) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265. (d) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 273. (e) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 1206. See also: (f) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
87. + see: (b) Masson, S.; Thuillier, A. Bull. Soc. Chim. Fr. 1969, 4368. (c) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265. (d) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 273. (e) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 1206. See also: (f) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
88. + see: (b) Masson, S.; Thuillier, A. Bull. Soc. Chim. Fr. 1969, 4368. (c) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265. (d) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 273. (e) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 1206. See also: (f) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
89. + see: (b) Masson, S.; Thuillier, A. Bull. Soc. Chim. Fr. 1969, 4368. (c) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265. (d) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 273. (e) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 1206. See also: (f) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
90. + see: (b) Masson, S.; Thuillier, A. Bull. Soc. Chim. Fr. 1969, 4368. (c) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265. (d) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 273. (e) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 1206. See also: (f) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
91. + see: (b) Masson, S.; Thuillier, A. Bull. Soc. Chim. Fr. 1969, 4368. (c) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265. (d) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 273. (e) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 1206. See also: (f) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
92. 2-Methylenenorborn-1-yl triflate 16a(OTf) is able to react with m-CPBA under more energetic conditions (refluxing methylene dichloride) to yield the corresponding nonrearranged spiranic oxirane as a mixture of epimers: García Martínez, A.; Teso Vilar, E.; García Fraile, A.; de la Moya Cerero, S.; Lora Maroto, B.; Diaz Morillo, C. Tetrahedron Lett. 2001, 42, 8293.
93. Both enantiopure 10-bromocamphor [10a(Br)] and 10-hydroxycamphor [10a(OH)] have been previously prepared from 10-camphorsulfonic acid in a very low overall yield (20% and 12%, respectively) according to the procedure described by Dallacker in ref 21. Alcohol 10a(OH) can be also prepared in 72% yield from β-pinene oxide (Villemin, D.; Hammandi, M. Synth. Commun. 1995, 25, 3141).
94. García Martínez, A.; Teso Vilar, E.; García Fraile, A.; de la Moya Cerero, S.; Lora Maroto, B. Tetrahedron: Asymmetry 2002, 13, 17.
95. For the enantiospecific synthesis oftrifiates 8a and 8b, we have used a variant of the standard procedure previously described by us (Garcìa Martínez, A.; Teso Vilar, E.; Osío Barcina, J.; Rodríguez Herrero, M. E.; de la Moya Cerero, S.; Hanack, M.; Subramanian, L. R. Tetrahedron: Asymmetry 1993, 4, 2333), consisting of the use of triisobutylamine as the nonnucleophilic base instead of N,N-diisobutyl2,4-dimethyl-3-pentanamine, which is no longer commercially available.
96. García Martínez, A.; Teso Vilar, E.; Garcia Fraile, A.; Ruano Franco, C.; Soto Salvador, J.; Subramanian, L. R.; Hanack, M. Synthesis 1987, 321.
97. Since the starting commercial (-)-fenchone (2) has an ee of 82%, all products enantiospecifically obtained from it [i.e. 8b, 9b, and 10b] must possess the same opticaly purity. This fact has been tested for the case of 10b(OH), by comparison of the obtained specific optical rotation with the measured one for enantiopure 10-hydroxyfenchone (see ref 32b).
98. Enantiopure 10a has been previously prepared from 10camphorsulfonyl chloride (Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 7, 3553).
99. 10-Hydroxyfenchone has been previously prepared from fenchone following a six-step route with low overall yield: (a) Paquette, L. A.; Teleha, C. A.; Taylos, R. T.; Maynard, G. D.; Rogers, R. D.; Gallucci, J. C.; Springer, J. P. J. Am. Chem. Soc. 1990, 112, 265 and references therein. Enantiopure 10-hydroxyfenchone has been described as the major metabolite in the biotransformation of (+)camphor in rabbits: (b) Miyazawa, M.; Kameoka, H. Chem. Express 1988, 3, 503.
100. 10-Hydroxyfenchone has been previously prepared from fenchone following a six-step route with low overall yield: (a) Paquette, L. A.; Teleha, C. A.; Taylos, R. T.; Maynard, G. D.; Rogers, R. D.; Gallucci, J. C.; Springer, J. P. J. Am. Chem. Soc. 1990, 112, 265 and references therein. Enantiopure 10-hydroxyfenchone has been described as the major metabolite in the biotransformation of (+)camphor in rabbits: (b) Miyazawa, M.; Kameoka, H. Chem. Express 1988, 3, 503.