Lead tetraacetate mediated 'one-pot' multistage transformations on selected unsaturated 1,2-diols: The Wieland-Miescher series

Tetrahedron

Volumn 54, Issue 22, 1998, Pages 5949-5958

  Arseniyadis, Siméon ^a   Brondi Alves, Rosemeire ^a   Quilez Del Moral, José ^a   Yashunsky, Dmitry V ^a   Potier, Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CYCLOHEPTANE DERIVATIVE; CYCLOHEXANE DERIVATIVE; LEAD ACETATE; OCTANE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032575244     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00269-5     Document Type: Article

References (31)

1. 1. Arseniyadis, S.; Yashunsky, D. V.; Pereira de Freitas, R.; Munoz Dorado, M.; Potier, P.; Toupet, L. Tetrahedron 1996, 52, 12443-12458;
2. Arseniyadis, S.; Brondi Alves R.; Pereira de Freitas, R.; Muñoz-Dorado M.; Yashunsky, D. V.; Potier, P.; Toupet, L. Heterocycles 1997,46, 727-764.
3. 2. Tetrahedron Symposia-in-Print Number 62, Cascade Reactions, Ron Grigg, Ed. 1996, 52, 11385-11664 and references cited therein.
4. 3. For synthetic routes to enantiomerically pure cycloheptanones see: Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875-878; for racemic cycloheptenones see: Pak, C.S.; Kim, S.K. J. Org. Chem. 1990, 55, 1954-1957; Demole, E.; Enggist, P.; Borer, C. Helv. Chim. Acta 1971, 54, 1845-1864. For the synthesis of seven-membered ring containing compounds via cycloadditions or annelations see: Harmata, M. ; Jones, D. E. Tetrahedron Lett. 1996, 37, 783-786; Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400-6401. For the construction of seven-membered ring containing fused bicyclic[n,m,0]systems via olefin metathesis see: Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014.
5. 3. For synthetic routes to enantiomerically pure cycloheptanones see: Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875-878; for racemic cycloheptenones see: Pak, C.S.; Kim, S.K. J. Org. Chem. 1990, 55, 1954-1957; Demole, E.; Enggist, P.; Borer, C. Helv. Chim. Acta 1971, 54, 1845-1864. For the synthesis of seven-membered ring containing compounds via cycloadditions or annelations see: Harmata, M. ; Jones, D. E. Tetrahedron Lett. 1996, 37, 783-786; Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400-6401. For the construction of seven-membered ring containing fused bicyclic[n,m,0]systems via olefin metathesis see: Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014.
6. 3. For synthetic routes to enantiomerically pure cycloheptanones see: Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875-878; for racemic cycloheptenones see: Pak, C.S.; Kim, S.K. J. Org. Chem. 1990, 55, 1954-1957; Demole, E.; Enggist, P.; Borer, C. Helv. Chim. Acta 1971, 54, 1845-1864. For the synthesis of seven-membered ring containing compounds via cycloadditions or annelations see: Harmata, M. ; Jones, D. E. Tetrahedron Lett. 1996, 37, 783-786; Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400-6401. For the construction of seven-membered ring containing fused bicyclic[n,m,0]systems via olefin metathesis see: Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014.
7. 3. For synthetic routes to enantiomerically pure cycloheptanones see: Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875-878; for racemic cycloheptenones see: Pak, C.S.; Kim, S.K. J. Org. Chem. 1990, 55, 1954-1957; Demole, E.; Enggist, P.; Borer, C. Helv. Chim. Acta 1971, 54, 1845-1864. For the synthesis of seven-membered ring containing compounds via cycloadditions or annelations see: Harmata, M. ; Jones, D. E. Tetrahedron Lett. 1996, 37, 783-786; Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400-6401. For the construction of seven-membered ring containing fused bicyclic[n,m,0]systems via olefin metathesis see: Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014.
8. 3. For synthetic routes to enantiomerically pure cycloheptanones see: Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875-878; for racemic cycloheptenones see: Pak, C.S.; Kim, S.K. J. Org. Chem. 1990, 55, 1954-1957; Demole, E.; Enggist, P.; Borer, C. Helv. Chim. Acta 1971, 54, 1845-1864. For the synthesis of seven-membered ring containing compounds via cycloadditions or annelations see: Harmata, M. ; Jones, D. E. Tetrahedron Lett. 1996, 37, 783-786; Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400-6401. For the construction of seven-membered ring containing fused bicyclic[n,m,0]systems via olefin metathesis see: Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014.
9. 3. For synthetic routes to enantiomerically pure cycloheptanones see: Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875-878; for racemic cycloheptenones see: Pak, C.S.; Kim, S.K. J. Org. Chem. 1990, 55, 1954-1957; Demole, E.; Enggist, P.; Borer, C. Helv. Chim. Acta 1971, 54, 1845-1864. For the synthesis of seven-membered ring containing compounds via cycloadditions or annelations see: Harmata, M. ; Jones, D. E. Tetrahedron Lett. 1996, 37, 783-786; Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400-6401. For the construction of seven-membered ring containing fused bicyclic[n,m,0]systems via olefin metathesis see: Schneider, M. F.; Junga, H.; Blechert, S. Tetrahedron 1995, 51, 13003-13014.
10. 4. Arseniyadis, S.; Brondi Alves, R.; Yashunsky, D. V.; Wang, Q.; Potier, P. Tetrahedron Lett. 1995, 36, 1027-1030.
11. 5. For leading references concerning the oxidative cleavage of 1,2-glycols, see: Shing, T. K. in Comprehensive Organic Synthesis, 1991, 7, 703-716, Ed. Ley, S. V., Pergamon Press; Malaprade, M. L. Bull. Soc. Chim. Fr. 1928, 43, 683-696; Rigby, W. J. Chem. Soc. 1950, 1907-1913; Criegee, R. Chem. Ber. 1931, 64, 260-266.
12. 5. For leading references concerning the oxidative cleavage of 1,2-glycols, see: Shing, T. K. in Comprehensive Organic Synthesis, 1991, 7, 703-716, Ed. Ley, S. V., Pergamon Press; Malaprade, M. L. Bull. Soc. Chim. Fr. 1928, 43, 683-696; Rigby, W. J. Chem. Soc. 1950, 1907-1913; Criegee, R. Chem. Ber. 1931, 64, 260-266.
13. 5. For leading references concerning the oxidative cleavage of 1,2-glycols, see: Shing, T. K. in Comprehensive Organic Synthesis, 1991, 7, 703-716, Ed. Ley, S. V., Pergamon Press; Malaprade, M. L. Bull. Soc. Chim. Fr. 1928, 43, 683-696; Rigby, W. J. Chem. Soc. 1950, 1907-1913; Criegee, R. Chem. Ber. 1931, 64, 260-266.
14. 5. For leading references concerning the oxidative cleavage of 1,2-glycols, see: Shing, T. K. in Comprehensive Organic Synthesis, 1991, 7, 703-716, Ed. Ley, S. V., Pergamon Press; Malaprade, M. L. Bull. Soc. Chim. Fr. 1928, 43, 683-696; Rigby, W. J. Chem. Soc. 1950, 1907-1913; Criegee, R. Chem. Ber. 1931, 64, 260-266.
15. 6. Rubottom, G. M. Oxidation in Organic Chemistry, Trahanovsky, Part D, Chapter I, Academic Press, Inc. 1982.
16. 7. Arseniyadis, S.; Rodriguez, R.; Muñoz Dorado, M.; Brondi Alves, R.; Ouazzani, J.; Ourisson, G. Tetrahedron, 1994, 50, 8399-8426; Hajos, Z. G.; Parrish, D. R. J. Org. Chem., 1974, 39, 1615-1621; Wieland, P.; Miescher, K. Helv. Chim. Acta, 1950, 53, 2215; Cohen, N. Accounts of Chemical Research 1976, 9, 412-417 and references cited therein.
17. 7. Arseniyadis, S.; Rodriguez, R.; Muñoz Dorado, M.; Brondi Alves, R.; Ouazzani, J.; Ourisson, G. Tetrahedron, 1994, 50, 8399-8426; Hajos, Z. G.; Parrish, D. R. J. Org. Chem., 1974, 39, 1615-1621; Wieland, P.; Miescher, K. Helv. Chim. Acta, 1950, 53, 2215; Cohen, N. Accounts of Chemical Research 1976, 9, 412-417 and references cited therein.
18. 7. Arseniyadis, S.; Rodriguez, R.; Muñoz Dorado, M.; Brondi Alves, R.; Ouazzani, J.; Ourisson, G. Tetrahedron, 1994, 50, 8399-8426; Hajos, Z. G.; Parrish, D. R. J. Org. Chem., 1974, 39, 1615-1621; Wieland, P.; Miescher, K. Helv. Chim. Acta, 1950, 53, 2215; Cohen, N. Accounts of Chemical Research 1976, 9, 412-417 and references cited therein.
19. 7. Arseniyadis, S.; Rodriguez, R.; Muñoz Dorado, M.; Brondi Alves, R.; Ouazzani, J.; Ourisson, G. Tetrahedron, 1994, 50, 8399-8426; Hajos, Z. G.; Parrish, D. R. J. Org. Chem., 1974, 39, 1615-1621; Wieland, P.; Miescher, K. Helv. Chim. Acta, 1950, 53, 2215; Cohen, N. Accounts of Chemical Research 1976, 9, 412-417 and references cited therein.
20. 8. There is literature precedent for such bis-hetero Diels-Alder reaction. For condensation of hexafluoroacetone with α,β-unsaturated compounds (acrolein) leading in high yields to bis(trifluoromethyl)-1,3-dioxins see: Fokin, A. V.; Kolomiets, A. F.; Krolevets, A. A. Izv. Akad. Nauk SSSR Ser. Khim. 1978, 976 (Chem. Abstr. 1978, 89 24232r).
21. 8. There is literature precedent for such bis-hetero Diels-Alder reaction. For condensation of hexafluoroacetone with α,β-unsaturated compounds (acrolein) leading in high yields to bis(trifluoromethyl)-1,3-dioxins see: Fokin, A. V.; Kolomiets, A. F.; Krolevets, A. A. Izv. Akad. Nauk SSSR Ser. Khim. 1978, 976 (Chem. Abstr. 1978, 89 24232r).
22. + : Arseniyadis, S; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
23. + : Arseniyadis, S; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
24. + : Arseniyadis, S; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
25. + : Arseniyadis, S; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
26. + : Arseniyadis, S; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
27. + : Arseniyadis, S; Sartoretti, J. Tetrahedron Lett. 1985, 26, 729-732.
28. 2+, Latimer states a value of 1.7V: Latimer, W. M. "The oxidation states of the elements and their potentials in aqueous solutions", Prentice Hall, N. Y., 1952.
29. 11. Brown, H. C.; Fletcher, R. S.; Johannesen, R. B. J. Am. Chem. Soc. 1951, 73, 212-221.
30. 12. The stereochemistry of 8 was established by ID NOEDIFF experiments. Strong two-way n.O.e. 's were observed between the bridghead hydrogen at C-5 and the angular methyl group at C-10a thus clearly establishing the cis fusion of the bicyclic ring system. Furthermore, the cis relationship of the C-10a angular methyl and C-4, C-5, C-9βax, C-1βeq hydrogens as well as the spatial proximities of C-5 hydrogen to C-7βax, C-4 hydrogens and the C-10a methyl group were easily established by the appropriate experiments thus allowing unambiguous assignment of C-2, C-4 stereochemistries.
31. 13. Zhu, P. C.; Lin, J.; Pittman, Jr, C. U. J. Org. Chem. 1995, 60, 5729-5731 and references cited therein.