Polyhydroxylated perhydro-1H-benz[e]indenyl derivatives with two angular 3a,5a-carbaldehyde moieties

Synlett

Volumn , Issue 11, 1999, Pages 1731-1734

  Mosimann, Hervé ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

7 oxabicyclo 2.2.1 heptane; Epoxydation; Photoreduction; Pinacolic rearrangement; Polyhydroxyperhydrophenanthrene

Indexed keywords

ALDEHYDE; BROMINE; EPOXIDE; HEPTANE; INDENE DERIVATIVE; PHENANTHRENE DERIVATIVE; ZINC;

ARTICLE; DEBROMINATION; EPOXIDATION; HYDROXYLATION; REACTION ANALYSIS;

EID: 0032704104     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2924     Document Type: Article

References (50)

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17. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
18. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
19. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
20. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
21. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
22. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
23. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
24. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
25. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
26. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
27. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
28. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
29. For related 1,2-shifts of electron-withdrawing groups such as RCO groups, see e.g.: Eschenmoser, A.; Schinz, H.; Fischer, R.; Colonge, R. Helv. Chim. Acta 1951, 34, 2329; House, H. O. J. Am. Chem. Soc. 1954, 76, 1235; Domagala, J. M.; Bach, R. D. J. Am. Chem. Soc. 1979, 101, 3118; Domagala, J. M.; Bach, R. D. J. Org. Chem. 1979, 44, 2429; Kunisch, F.; Hobert, K.; Welzel, P. Tetrahedron Lett. 1985, 26, 6039; Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580; Alessandri, P.; De Angelis, F.; Gambacorta, A. Tetrahedron 1985, 41, 2831; Peters, J. A.; van der Toorn, J. M.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1975, 94, 122; Hart, H.; Huang, I.; Lavrik, P. J. Org. Chem. 1974, 39, 999; Hart, H.; Shih, E. M. J. Org. Chem. 1975, 40, 1128; Zaidi, J. H.; Waring, A. J. J. Chem. Soc., Chem. Commun. 1980, 618; Shubin, V. G. in "Topics in Current Chemistry" Springer Verlag, Berlin, 1984, 117, 267; see also: Vogel, P. Chimica Oggi 1997, 15, 37.
30. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155; Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
31. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155; Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
32. C: 208.0, 204.7, 170.3 (3s), 85.9, 82.0, 81.0, 78.9 (4d), 66.4 (t), 63.6 (s), 54.1, 48.5, 45.9 (3d), 48.4 (s), 43.3, 41.5, 32.2 (3t), 20.7 (q).
33. 1H-NMR spectra (NOESY, COSY).
34. C: 209.2, 205.4, 169.2, 88.7 (4s), 83.0, 82.3, 81.5, 79.3 (4d), 73.0 (t), 72.0, 54.0, 48.6 (3d), 50.0 (s), 46.4, 40.9, 33.8 (3t), 21.4 (q).
35. For related reactions in which cyclic ethers are formed by participation of acetoxymethyl groups to heterolytic processes, see ref. 10 and: Jotterand, N.; Vogel, P.; Schenk, K. Helv. Chim. Acta 1999, 82, 821.
36. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
37. 3) δC: 208.4, 205.1 (2s), 138.8 (d), 116.4 (t), 87.0, 81.8, 81.2, 78.8 (4d), 63.8 (s), 54.1 (d), 50.7 (s), 48.6, 45.5 (2d), 43.2, 41.3, 34.5 (3t).
38. C: 207.2, 199.7, 177.3 (3s), 137.4(d), 118.0(t), 97.9, 87.9, 81.3, 77.3, 63.8 (5d), 60.9 (s), 51.8 (d), 48.7 (s), 46.8, 43.2 (2t), 42.9 (d), 38.7, 38.5 (2s), 35.4 (t), 27.1, 26.6 (2q).
39. Cossy, J.; Aclinou, P.; Bellosta, V.; Furet, N.; Baranne-Lafont, J.; Sparfel, D.; Souchaud, C. Tetrahedron Lett. 1991, 32, 1315; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. J. Org. Chem. 1995, 60, 8351; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V. Tetrahedron Lett. 1995, 36, 2067.
40. Cossy, J.; Aclinou, P.; Bellosta, V.; Furet, N.; Baranne-Lafont, J.; Sparfel, D.; Souchaud, C. Tetrahedron Lett. 1991, 32, 1315; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. J. Org. Chem. 1995, 60, 8351; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V. Tetrahedron Lett. 1995, 36, 2067.
41. Cossy, J.; Aclinou, P.; Bellosta, V.; Furet, N.; Baranne-Lafont, J.; Sparfel, D.; Souchaud, C. Tetrahedron Lett. 1991, 32, 1315; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. J. Org. Chem. 1995, 60, 8351; Cossy, J.; Ranaivosata, J.-L.; Bellosta, V. Tetrahedron Lett. 1995, 36, 2067.
42. C: 206.7, 202.3, 177.8, 176.4 (4s), 143.8 (d), 116.7 (t), 96.5, 80.5, 68.4, 63.1 (4d), 63.0 (s), 45.7, 45.3, 44.6 (3t), 45.1, 41.1 (2d), 40.5, 38.8, 38.7 (3s), 38.3 (t), 27.1, 26.7 (2q).
43. +), 377 (7), 276 (18), 275 (100).
44. Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865; Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979; Forster, A.; Kovac, T.; Mosimann, H.; Renaud, P. Vogel, P. Tetrahedron: Asymmetry 1999, 10, 567.
45. Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865; Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979; Forster, A.; Kovac, T.; Mosimann, H.; Renaud, P. Vogel, P. Tetrahedron: Asymmetry 1999, 10, 567.
46. Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865; Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979; Forster, A.; Kovac, T.; Mosimann, H.; Renaud, P. Vogel, P. Tetrahedron: Asymmetry 1999, 10, 567.
47. Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865; Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979; Forster, A.; Kovac, T.; Mosimann, H.; Renaud, P. Vogel, P. Tetrahedron: Asymmetry 1999, 10, 567.
48. Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865; Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979; Forster, A.; Kovac, T.; Mosimann, H.; Renaud, P. Vogel, P. Tetrahedron: Asymmetry 1999, 10, 567.
49. Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865; Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979; Forster, A.; Kovac, T.; Mosimann, H.; Renaud, P. Vogel, P. Tetrahedron: Asymmetry 1999, 10, 567.
50. Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865; Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389; Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729; Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173; Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75; Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979; Forster, A.; Kovac, T.; Mosimann, H.; Renaud, P. Vogel, P. Tetrahedron: Asymmetry 1999, 10, 567.