Formation of quaternary centres via iron allyl cations. Rapid entry into spirocyclic ring systems

Canadian Journal of Chemistry

Volumn 75, Issue 7, 1997, Pages 965-974

  Charlton, M Anne ^a   Green, James R ^a  

^a UNIVERSITY OF WINDSOR   (Canada)

Author keywords

1,6 dicarbonyls; Allyliron complexes; Spirocycle synthesis; Umpolung synthesis

Indexed keywords

CONDENSATION REACTIONS; CONFORMATIONS; ESTERS; ETHERS; IRON COMPOUNDS; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL);

ALLYLIRON COMPLEXES; SPIROCYCLE SYNTHESIS; UMPOLUNG SYNTHESIS;

ORGANOMETALLICS;

ACETAL; ESTER; ETHER; IRON DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0031194043     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v97-116     Document Type: Article

References (51)

1. S. Danishefsky. Acc. Chem. Res. 12, 66 (1979); H.N.C. Wong, H.-Y. Hon, C.-W. Tse, J. Tanko, and T. Hudlicky. Chem. Rev. 89, 165 (1989); H.C. Brown and H. Nambu. J. Am. Chem. Soc. 92, 1761 (1970); T. Ibuka and H. Minakata. Synth. Commun. 10, 119 (1980); J. Tsuji, H. Ueno, Y. Kobayashi, and H. Okumoto. Tetrahedron Lett. 22, 2573 (1981); A.J. Pearson. Chem. Ind. 742 (1982); P. Prempree, S. Radviroongit, and Y. Thebtaranonth. J. Org. Chem. 48, 3553 (1983); F. Orsini and F. Pelizzoni. Synth. Commun. 13, 523 (1983); B.M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 3167 (1994).
2. S. Danishefsky. Acc. Chem. Res. 12, 66 (1979); H.N.C. Wong, H.-Y. Hon, C.-W. Tse, J. Tanko, and T. Hudlicky. Chem. Rev. 89, 165 (1989); H.C. Brown and H. Nambu. J. Am. Chem. Soc. 92, 1761 (1970); T. Ibuka and H. Minakata. Synth. Commun. 10, 119 (1980); J. Tsuji, H. Ueno, Y. Kobayashi, and H. Okumoto. Tetrahedron Lett. 22, 2573 (1981); A.J. Pearson. Chem. Ind. 742 (1982); P. Prempree, S. Radviroongit, and Y. Thebtaranonth. J. Org. Chem. 48, 3553 (1983); F. Orsini and F. Pelizzoni. Synth. Commun. 13, 523 (1983); B.M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 3167 (1994).
3. S. Danishefsky. Acc. Chem. Res. 12, 66 (1979); H.N.C. Wong, H.-Y. Hon, C.-W. Tse, J. Tanko, and T. Hudlicky. Chem. Rev. 89, 165 (1989); H.C. Brown and H. Nambu. J. Am. Chem. Soc. 92, 1761 (1970); T. Ibuka and H. Minakata. Synth. Commun. 10, 119 (1980); J. Tsuji, H. Ueno, Y. Kobayashi, and H. Okumoto. Tetrahedron Lett. 22, 2573 (1981); A.J. Pearson. Chem. Ind. 742 (1982); P. Prempree, S. Radviroongit, and Y. Thebtaranonth. J. Org. Chem. 48, 3553 (1983); F. Orsini and F. Pelizzoni. Synth. Commun. 13, 523 (1983); B.M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 3167 (1994).
4. S. Danishefsky. Acc. Chem. Res. 12, 66 (1979); H.N.C. Wong, H.-Y. Hon, C.-W. Tse, J. Tanko, and T. Hudlicky. Chem. Rev. 89, 165 (1989); H.C. Brown and H. Nambu. J. Am. Chem. Soc. 92, 1761 (1970); T. Ibuka and H. Minakata. Synth. Commun. 10, 119 (1980); J. Tsuji, H. Ueno, Y. Kobayashi, and H. Okumoto. Tetrahedron Lett. 22, 2573 (1981); A.J. Pearson. Chem. Ind. 742 (1982); P. Prempree, S. Radviroongit, and Y. Thebtaranonth. J. Org. Chem. 48, 3553 (1983); F. Orsini and F. Pelizzoni. Synth. Commun. 13, 523 (1983); B.M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 3167 (1994).
5. S. Danishefsky. Acc. Chem. Res. 12, 66 (1979); H.N.C. Wong, H.-Y. Hon, C.-W. Tse, J. Tanko, and T. Hudlicky. Chem. Rev. 89, 165 (1989); H.C. Brown and H. Nambu. J. Am. Chem. Soc. 92, 1761 (1970); T. Ibuka and H. Minakata. Synth. Commun. 10, 119 (1980); J. Tsuji, H. Ueno, Y. Kobayashi, and H. Okumoto. Tetrahedron Lett. 22, 2573 (1981); A.J. Pearson. Chem. Ind. 742 (1982); P. Prempree, S. Radviroongit, and Y. Thebtaranonth. J. Org. Chem. 48, 3553 (1983); F. Orsini and F. Pelizzoni. Synth. Commun. 13, 523 (1983); B.M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 3167 (1994).
6. S. Danishefsky. Acc. Chem. Res. 12, 66 (1979); H.N.C. Wong, H.-Y. Hon, C.-W. Tse, J. Tanko, and T. Hudlicky. Chem. Rev. 89, 165 (1989); H.C. Brown and H. Nambu. J. Am. Chem. Soc. 92, 1761 (1970); T. Ibuka and H. Minakata. Synth. Commun. 10, 119 (1980); J. Tsuji, H. Ueno, Y. Kobayashi, and H. Okumoto. Tetrahedron Lett. 22, 2573 (1981); A.J. Pearson. Chem. Ind. 742 (1982); P. Prempree, S. Radviroongit, and Y. Thebtaranonth. J. Org. Chem. 48, 3553 (1983); F. Orsini and F. Pelizzoni. Synth. Commun. 13, 523 (1983); B.M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 3167 (1994).
7. S. Danishefsky. Acc. Chem. Res. 12, 66 (1979); H.N.C. Wong, H.-Y. Hon, C.-W. Tse, J. Tanko, and T. Hudlicky. Chem. Rev. 89, 165 (1989); H.C. Brown and H. Nambu. J. Am. Chem. Soc. 92, 1761 (1970); T. Ibuka and H. Minakata. Synth. Commun. 10, 119 (1980); J. Tsuji, H. Ueno, Y. Kobayashi, and H. Okumoto. Tetrahedron Lett. 22, 2573 (1981); A.J. Pearson. Chem. Ind. 742 (1982); P. Prempree, S. Radviroongit, and Y. Thebtaranonth. J. Org. Chem. 48, 3553 (1983); F. Orsini and F. Pelizzoni. Synth. Commun. 13, 523 (1983); B.M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 3167 (1994).
8. S. Danishefsky. Acc. Chem. Res. 12, 66 (1979); H.N.C. Wong, H.-Y. Hon, C.-W. Tse, J. Tanko, and T. Hudlicky. Chem. Rev. 89, 165 (1989); H.C. Brown and H. Nambu. J. Am. Chem. Soc. 92, 1761 (1970); T. Ibuka and H. Minakata. Synth. Commun. 10, 119 (1980); J. Tsuji, H. Ueno, Y. Kobayashi, and H. Okumoto. Tetrahedron Lett. 22, 2573 (1981); A.J. Pearson. Chem. Ind. 742 (1982); P. Prempree, S. Radviroongit, and Y. Thebtaranonth. J. Org. Chem. 48, 3553 (1983); F. Orsini and F. Pelizzoni. Synth. Commun. 13, 523 (1983); B.M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 3167 (1994).
9. S. Danishefsky. Acc. Chem. Res. 12, 66 (1979); H.N.C. Wong, H.-Y. Hon, C.-W. Tse, J. Tanko, and T. Hudlicky. Chem. Rev. 89, 165 (1989); H.C. Brown and H. Nambu. J. Am. Chem. Soc. 92, 1761 (1970); T. Ibuka and H. Minakata. Synth. Commun. 10, 119 (1980); J. Tsuji, H. Ueno, Y. Kobayashi, and H. Okumoto. Tetrahedron Lett. 22, 2573 (1981); A.J. Pearson. Chem. Ind. 742 (1982); P. Prempree, S. Radviroongit, and Y. Thebtaranonth. J. Org. Chem. 48, 3553 (1983); F. Orsini and F. Pelizzoni. Synth. Commun. 13, 523 (1983); B.M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 3167 (1994).
10. J.R. Green and M.K. Carroll. Tetrahedron Lett. 32, 141 (1991); T. Zhou and J.R. Green. Tetrahedron Lett. 34, 4497 (1993); C.S. Vizniowski, J.R. Green, and T.L. Breen, and A.V. Dalacu. J. Org. Chem. 60, 7496 (1995).
11. J.R. Green and M.K. Carroll. Tetrahedron Lett. 32, 141 (1991); T. Zhou and J.R. Green. Tetrahedron Lett. 34, 4497 (1993); C.S. Vizniowski, J.R. Green, and T.L. Breen, and A.V. Dalacu. J. Org. Chem. 60, 7496 (1995).
12. J.R. Green and M.K. Carroll. Tetrahedron Lett. 32, 141 (1991); T. Zhou and J.R. Green. Tetrahedron Lett. 34, 4497 (1993); C.S. Vizniowski, J.R. Green, and T.L. Breen, and A.V. Dalacu. J. Org. Chem. 60, 7496 (1995).
13. J.R. Green and W.A. Donaldson. In Encyclopedia of inorganic chemistry. Vol. 4. Edited by R.B. King. John Wiley and Sons, New York. 1994. pp. 1735-1784; A.J. Pearson. Iron compounds in organic synthesis. Academic Press, London. 1994. Chap. 3.
14. J.R. Green and W.A. Donaldson. In Encyclopedia of inorganic chemistry. Vol. 4. Edited by R.B. King. John Wiley and Sons, New York. 1994. pp. 1735-1784; A.J. Pearson. Iron compounds in organic synthesis. Academic Press, London. 1994. Chap. 3.
15. D. Enders and M. Finkam. Synlett, 401 (1993); Liebigs Ann. Chem. 551 (1993); D. Enders, B. Jandeleit, and G. Raabe. Angew. Chem. Int. Ed. Engl. 3, 1949 (1994); D. Enders and B. Jandeleit. Synthesis, 1327 (1994); D. Enders, B. Jandeleit, and O.F. Prokopenko. Tetrahedron, 51, 6273 (1995); D. Enders, S. von Berg, and B. Jandeleit. Synlett, 18 (1996); D. Enders, P. Fey, T. Schmitz, B.B. Lohray, and B. Jandeleit. J. Organomet. Chem. 514, 227 (1996); D. Enders, U. Frank, P. Fey, B. Jandeleit, and B.B. Lohray. J. Organomet. Chem. 519, 147 (1996).
16. D. Enders and M. Finkam. Synlett, 401 (1993); Liebigs Ann. Chem. 551 (1993); D. Enders, B. Jandeleit, and G. Raabe. Angew. Chem. Int. Ed. Engl. 3, 1949 (1994); D. Enders and B. Jandeleit. Synthesis, 1327 (1994); D. Enders, B. Jandeleit, and O.F. Prokopenko. Tetrahedron, 51, 6273 (1995); D. Enders, S. von Berg, and B. Jandeleit. Synlett, 18 (1996); D. Enders, P. Fey, T. Schmitz, B.B. Lohray, and B. Jandeleit. J. Organomet. Chem. 514, 227 (1996); D. Enders, U. Frank, P. Fey, B. Jandeleit, and B.B. Lohray. J. Organomet. Chem. 519, 147 (1996).
17. D. Enders and M. Finkam. Synlett, 401 (1993); Liebigs Ann. Chem. 551 (1993); D. Enders, B. Jandeleit, and G. Raabe. Angew. Chem. Int. Ed. Engl. 3, 1949 (1994); D. Enders and B. Jandeleit. Synthesis, 1327 (1994); D. Enders, B. Jandeleit, and O.F. Prokopenko. Tetrahedron, 51, 6273 (1995); D. Enders, S. von Berg, and B. Jandeleit. Synlett, 18 (1996); D. Enders, P. Fey, T. Schmitz, B.B. Lohray, and B. Jandeleit. J. Organomet. Chem. 514, 227 (1996); D. Enders, U. Frank, P. Fey, B. Jandeleit, and B.B. Lohray. J. Organomet. Chem. 519, 147 (1996).
18. D. Enders and M. Finkam. Synlett, 401 (1993); Liebigs Ann. Chem. 551 (1993); D. Enders, B. Jandeleit, and G. Raabe. Angew. Chem. Int. Ed. Engl. 3, 1949 (1994); D. Enders and B. Jandeleit. Synthesis, 1327 (1994); D. Enders, B. Jandeleit, and O.F. Prokopenko. Tetrahedron, 51, 6273 (1995); D. Enders, S. von Berg, and B. Jandeleit. Synlett, 18 (1996); D. Enders, P. Fey, T. Schmitz, B.B. Lohray, and B. Jandeleit. J. Organomet. Chem. 514, 227 (1996); D. Enders, U. Frank, P. Fey, B. Jandeleit, and B.B. Lohray. J. Organomet. Chem. 519, 147 (1996).
19. D. Enders and M. Finkam. Synlett, 401 (1993); Liebigs Ann. Chem. 551 (1993); D. Enders, B. Jandeleit, and G. Raabe. Angew. Chem. Int. Ed. Engl. 3, 1949 (1994); D. Enders and B. Jandeleit. Synthesis, 1327 (1994); D. Enders, B. Jandeleit, and O.F. Prokopenko. Tetrahedron, 51, 6273 (1995); D. Enders, S. von Berg, and B. Jandeleit. Synlett, 18 (1996); D. Enders, P. Fey, T. Schmitz, B.B. Lohray, and B. Jandeleit. J. Organomet. Chem. 514, 227 (1996); D. Enders, U. Frank, P. Fey, B. Jandeleit, and B.B. Lohray. J. Organomet. Chem. 519, 147 (1996).
20. D. Enders and M. Finkam. Synlett, 401 (1993); Liebigs Ann. Chem. 551 (1993); D. Enders, B. Jandeleit, and G. Raabe. Angew. Chem. Int. Ed. Engl. 3, 1949 (1994); D. Enders and B. Jandeleit. Synthesis, 1327 (1994); D. Enders, B. Jandeleit, and O.F. Prokopenko. Tetrahedron, 51, 6273 (1995); D. Enders, S. von Berg, and B. Jandeleit. Synlett, 18 (1996); D. Enders, P. Fey, T. Schmitz, B.B. Lohray, and B. Jandeleit. J. Organomet. Chem. 514, 227 (1996); D. Enders, U. Frank, P. Fey, B. Jandeleit, and B.B. Lohray. J. Organomet. Chem. 519, 147 (1996).
21. D. Enders and M. Finkam. Synlett, 401 (1993); Liebigs Ann. Chem. 551 (1993); D. Enders, B. Jandeleit, and G. Raabe. Angew. Chem. Int. Ed. Engl. 3, 1949 (1994); D. Enders and B. Jandeleit. Synthesis, 1327 (1994); D. Enders, B. Jandeleit, and O.F. Prokopenko. Tetrahedron, 51, 6273 (1995); D. Enders, S. von Berg, and B. Jandeleit. Synlett, 18 (1996); D. Enders, P. Fey, T. Schmitz, B.B. Lohray, and B. Jandeleit. J. Organomet. Chem. 514, 227 (1996); D. Enders, U. Frank, P. Fey, B. Jandeleit, and B.B. Lohray. J. Organomet. Chem. 519, 147 (1996).
22. D. Enders and M. Finkam. Synlett, 401 (1993); Liebigs Ann. Chem. 551 (1993); D. Enders, B. Jandeleit, and G. Raabe. Angew. Chem. Int. Ed. Engl. 3, 1949 (1994); D. Enders and B. Jandeleit. Synthesis, 1327 (1994); D. Enders, B. Jandeleit, and O.F. Prokopenko. Tetrahedron, 51, 6273 (1995); D. Enders, S. von Berg, and B. Jandeleit. Synlett, 18 (1996); D. Enders, P. Fey, T. Schmitz, B.B. Lohray, and B. Jandeleit. J. Organomet. Chem. 514, 227 (1996); D. Enders, U. Frank, P. Fey, B. Jandeleit, and B.B. Lohray. J. Organomet. Chem. 519, 147 (1996).
23. W.J. Koot, H. Hiemstra, and W.N. Speckamp. J. Chem. Soc. Chem. Commun., 156 (1993); J.C.P. Hopman, H. Hiemstra, and W.N. Speckamp. J. Chem. Soc. Chem. Commun. 617 (1995).
24. W.J. Koot, H. Hiemstra, and W.N. Speckamp. J. Chem. Soc. Chem. Commun., 156 (1993); J.C.P. Hopman, H. Hiemstra, and W.N. Speckamp. J. Chem. Soc. Chem. Commun. 617 (1995).
25. J.C.P. Hopman. Ph.D. Dissertation. University of Amsterdam. 1996.
26. W.G. Dauben and D.J. Hart. J. Am. Chem. Soc. 99, 7307 (1977).
27. Y. Kita, J. Segawa, J. Haruta, H. Yashuda, and Y. Tamura. J. Chem. Soc. Perkin Trans, 1, 1099 (1982).
28. N.D.A. Walshe, G.B.T. Goodwin, G.C. Smith, and F.E. Woodward. Org. Synth. 65, 1 (1987).
29. N. Leonard and D. Felley. J. Am. Chem. Soc. 72, 2537 (1950).
30. D.A. Evans. In Asymmetric synthesis. Vol. 3. Edited by J.D. Morrison. Academic Press, Orlando, Fla. 1984. Chap. 1; A.P. Krapcho and E.A. Dundulis. J. Org. Chem. 45, 3236 (1980).
31. D.A. Evans. In Asymmetric synthesis. Vol. 3. Edited by J.D. Morrison. Academic Press, Orlando, Fla. 1984. Chap. 1; A.P. Krapcho and E.A. Dundulis. J. Org. Chem. 45, 3236 (1980).
32. E.-P. Krebs. Helv. Chim. Acta, 64, 1023 (1981); A.S. Kende and B.H. Toder. J. Org. Chem. 47, 167 (1982); J.R. Green. Ph.D. Thesis. University of Waterloo. 1987; P. Galatsis, J.J. Manwell, and S.D. Millan. Tetrahedron Lett. 37, 5261 (1996).
33. E.-P. Krebs. Helv. Chim. Acta, 64, 1023 (1981); A.S. Kende and B.H. Toder. J. Org. Chem. 47, 167 (1982); J.R. Green. Ph.D. Thesis. University of Waterloo. 1987; P. Galatsis, J.J. Manwell, and S.D. Millan. Tetrahedron Lett. 37, 5261 (1996).
34. E.-P. Krebs. Helv. Chim. Acta, 64, 1023 (1981); A.S. Kende and B.H. Toder. J. Org. Chem. 47, 167 (1982); J.R. Green. Ph.D. Thesis. University of Waterloo. 1987; P. Galatsis, J.J. Manwell, and S.D. Millan. Tetrahedron Lett. 37, 5261 (1996).
35. E.-P. Krebs. Helv. Chim. Acta, 64, 1023 (1981); A.S. Kende and B.H. Toder. J. Org. Chem. 47, 167 (1982); J.R. Green. Ph.D. Thesis. University of Waterloo. 1987; P. Galatsis, J.J. Manwell, and S.D. Millan. Tetrahedron Lett. 37, 5261 (1996).
36. R. Breiman and M. Avramoff. Isr. J. Chem. 9, 57 (1971); J.F. Tinker. J. Org. Chem. 16, 1417 (1951).
37. R. Breiman and M. Avramoff. Isr. J. Chem. 9, 57 (1971); J.F. Tinker. J. Org. Chem. 16, 1417 (1951).
38. J.J. Bloomfield, D.C. Owsley, and J.M. Nelke. Org. React. 23, 259 (1976).
39. T. Ibuka, K. Hayashi, H. Minakata, Y. Ito, and Y. Inubushi. Can. J. Chem. 57, 1579 (1979).
40. J.E. McMurry and M.P. Fleming. J. Am. Chem. Soc. 105, 1660 (1983); W. Li, Y. Li, and Y. Li. Chem. Lett. 741 (1994); Synthesis, 678 (1994).
41. J.E. McMurry and M.P. Fleming. J. Am. Chem. Soc. 105, 1660 (1983); W. Li, Y. Li, and Y. Li. Chem. Lett. 741 (1994); Synthesis, 678 (1994).
42. J.E. McMurry and M.P. Fleming. J. Am. Chem. Soc. 105, 1660 (1983); W. Li, Y. Li, and Y. Li. Chem. Lett. 741 (1994); Synthesis, 678 (1994).
43. P.J. Garegg and B. Samuelsson. J. Chem. Soc. Perkin Trans. 1, 2866 (1980).
44. M.P. Cooke, Jr. and I.N. Houpis. Tetrahedron Lett. 26, 4987 (1985); T. van der Does, G.W. Klumpp, and M. Schakel. Tetrahedron Lett. 27, 519 (1986); C.J. Flann and L.E. Overman. J. Am. Chem. Soc. 109, 6115 (1987).
45. M.P. Cooke, Jr. and I.N. Houpis. Tetrahedron Lett. 26, 4987 (1985); T. van der Does, G.W. Klumpp, and M. Schakel. Tetrahedron Lett. 27, 519 (1986); C.J. Flann and L.E. Overman. J. Am. Chem. Soc. 109, 6115 (1987).
46. M.P. Cooke, Jr. and I.N. Houpis. Tetrahedron Lett. 26, 4987 (1985); T. van der Does, G.W. Klumpp, and M. Schakel. Tetrahedron Lett. 27, 519 (1986); C.J. Flann and L.E. Overman. J. Am. Chem. Soc. 109, 6115 (1987).
47. J. Salaün and J. Marguerite. Org. Synth. 63, 147 (1984).
48. M.R. Winkle, J.M. Lasinger, and R.C. Ronald. J. Chem. Soc. Chem. Commun. 87 (1980).
49. W.C. Still, M. Kahn, and A. Mitra. J. Org. Chem. 43, 2923 (1978).
50. A. Asheroft, D. Davies, and J. Sutherland. Tetrahedron, 40, 4579 (1984).
51. P.A. Wender and A.W. White. J. Am. Chem. Soc. 110, 2218 (1988).