Intramolecular pauson-khand reactions of methylenecyclopropane and bicyclopropylidene derivatives as an approach to spiro(cyclopropanebicyclo[n.3. 0]alkenones)

Chemistry - A European Journal

Volumn 11, Issue 8, 2005, Pages 2471-2482

  De Meijere, Armin ^a   Becker, Heike ^a   Stolle, Andreas ^a   Kozhushkov, Sergei I ^a   Teresa Bes, M ^a,b   Salaüin, Jacques ^c   Noltemeyer, Mathias ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF ZARAGOZA   (Spain)

^c Institut de Chimie Moleculaire d'Orsay   (France)

Author keywords

Alkynes; Bicyclopropylidene; Cobalt; Cyclization; Cyclopropanes; Spiro compounds

Indexed keywords

ALCOHOLS; AROMATIC COMPOUNDS; CARBONYLATION; COBALT; CRYSTAL STRUCTURE; DERIVATIVES; OXYGEN; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; X RAY ANALYSIS;

ALKYNES; BICYCLOPROPYLIDENE; CYCLIZATION; CYCLOPROPANES; SPIRO COMPOUNDS;

REACTION KINETICS;

EID: 17444421205     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400997     Document Type: Article

References (77)

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32. [8e-h] have been reviewed extensively: a) P. Binger, H. M Buch, Top. Curr. Chem. 1987, 135, 77-151; b) P. Binger, T. Schmidt, in: Methods of Organic Chemistry, Vol. E 17c (Houben-Weyl) (Ed.: A. de Meijere), Thieme, Stuttgart, 1997, pp. 2217-2294; c) A. Brandi, A. Goti, Chem. Rev. 1998, 98, 589-635; d) A. Brandi, S. Cicchi, P.M. Cordero, A. Goti, Chem. Rev. 2003, 103, 1213-1269; e) A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Zh. Org. Khim. 1996, 32, 1607-1626; A. de Meijere, S.I. Kozhushkov, A.F. Khlebnikov, Russ. J. Org. Chem. (Engl. Transl.) 1996, 32, 1555-1575; f) A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Top. Curr. Chem. 2000, 207, 89-147 ; g) A. de Meijere, S. I. Kozhushkov, Eur. J. Org. Chem. 2000, 3809-3822; h) A. de Meijere, S. I. Kozhushkov, T. Späth, M. von Seebach, S. Löhr, H. Nüske, T. Pohlmann, M. Es-Sayed, S. Bräse, Pure Appl. Chem. 2000, 72, 1745-1756.
33. [8e-h] have been reviewed extensively: a) P. Binger, H. M Buch, Top. Curr. Chem. 1987, 135, 77-151; b) P. Binger, T. Schmidt, in: Methods of Organic Chemistry, Vol. E 17c (Houben-Weyl) (Ed.: A. de Meijere), Thieme, Stuttgart, 1997, pp. 2217-2294; c) A. Brandi, A. Goti, Chem. Rev. 1998, 98, 589-635; d) A. Brandi, S. Cicchi, P.M. Cordero, A. Goti, Chem. Rev. 2003, 103, 1213-1269; e) A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Zh. Org. Khim. 1996, 32, 1607-1626; A. de Meijere, S.I. Kozhushkov, A.F. Khlebnikov, Russ. J. Org. Chem. (Engl. Transl.) 1996, 32, 1555-1575; f) A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Top. Curr. Chem. 2000, 207, 89-147 ; g) A. de Meijere, S. I. Kozhushkov, Eur. J. Org. Chem. 2000, 3809-3822; h) A. de Meijere, S. I. Kozhushkov, T. Späth, M. von Seebach, S. Löhr, H. Nüske, T. Pohlmann, M. Es-Sayed, S. Bräse, Pure Appl. Chem. 2000, 72, 1745-1756.
34. [8e-h] have been reviewed extensively: a) P. Binger, H. M Buch, Top. Curr. Chem. 1987, 135, 77-151; b) P. Binger, T. Schmidt, in: Methods of Organic Chemistry, Vol. E 17c (Houben-Weyl) (Ed.: A. de Meijere), Thieme, Stuttgart, 1997, pp. 2217-2294; c) A. Brandi, A. Goti, Chem. Rev. 1998, 98, 589-635; d) A. Brandi, S. Cicchi, P.M. Cordero, A. Goti, Chem. Rev. 2003, 103, 1213-1269; e) A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Zh. Org. Khim. 1996, 32, 1607-1626; A. de Meijere, S.I. Kozhushkov, A.F. Khlebnikov, Russ. J. Org. Chem. (Engl. Transl.) 1996, 32, 1555-1575; f) A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Top. Curr. Chem. 2000, 207, 89-147 ; g) A. de Meijere, S. I. Kozhushkov, Eur. J. Org. Chem. 2000, 3809-3822; h) A. de Meijere, S. I. Kozhushkov, T. Späth, M. von Seebach, S. Löhr, H. Nüske, T. Pohlmann, M. Es-Sayed, S. Bräse, Pure Appl. Chem. 2000, 72, 1745-1756.
35. W. A. Smit, S. L. Kireev, O. M. Nefedov, V. A. Tarasov, Tetrahedron Lett. 1989, 30, 4021-4024.
36. Intermolecular PKRs: a) H. Corlay, I.W. James, E. Fouquet, J. Schmidt, W. B. Motherwell, Synlett 1996, 990-992; b) B. Witulski, T. Stengel, Angew. Chem. 1998, 110, 495-498; Angew. Chem. Int. Ed. Engl. 1998, 37, 489-492; intramolecular PKRs: c) S. Bräse, S. Schömenauer, G. McGaffin, A. Stolle, A. de Meijere, Chem. Eur, J. 1996, 2, 545-555; d) H. Corlay, E. Fouquet, E. Magnier, W.B. Motherwell, Chem. Commun. 1999, 183-184; e) M.E. Krafft, L.V.R. Boñaga, A. S. Felts, C. Hirosawa, S. Kerrigan, J. Org. Chem. 2003, 68, 6039-6042; f) M. E. Krafft, Z. Fu, L. V. R. Boñaga, Tetrahedron Lett. 2001, 42, 1427-1432; for a short review on inter- and intramolecular PKRs of 2 see also: g) A. Goti, F. M. Cordero, A. Brandi, Top. Curr. Chem. 1996, 178, 1-97.
37. Intermolecular PKRs: a) H. Corlay, I.W. James, E. Fouquet, J. Schmidt, W. B. Motherwell, Synlett 1996, 990-992; b) B. Witulski, T. Stengel, Angew. Chem. 1998, 110, 495-498; Angew. Chem. Int. Ed. Engl. 1998, 37, 489-492; intramolecular PKRs: c) S. Bräse, S. Schömenauer, G. McGaffin, A. Stolle, A. de Meijere, Chem. Eur, J. 1996, 2, 545-555; d) H. Corlay, E. Fouquet, E. Magnier, W.B. Motherwell, Chem. Commun. 1999, 183-184; e) M.E. Krafft, L.V.R. Boñaga, A. S. Felts, C. Hirosawa, S. Kerrigan, J. Org. Chem. 2003, 68, 6039-6042; f) M. E. Krafft, Z. Fu, L. V. R. Boñaga, Tetrahedron Lett. 2001, 42, 1427-1432; for a short review on inter- and intramolecular PKRs of 2 see also: g) A. Goti, F. M. Cordero, A. Brandi, Top. Curr. Chem. 1996, 178, 1-97.
38. Intermolecular PKRs: a) H. Corlay, I.W. James, E. Fouquet, J. Schmidt, W. B. Motherwell, Synlett 1996, 990-992; b) B. Witulski, T. Stengel, Angew. Chem. 1998, 110, 495-498; Angew. Chem. Int. Ed. Engl. 1998, 37, 489-492; intramolecular PKRs: c) S. Bräse, S. Schömenauer, G. McGaffin, A. Stolle, A. de Meijere, Chem. Eur, J. 1996, 2, 545-555; d) H. Corlay, E. Fouquet, E. Magnier, W.B. Motherwell, Chem. Commun. 1999, 183-184; e) M.E. Krafft, L.V.R. Boñaga, A. S. Felts, C. Hirosawa, S. Kerrigan, J. Org. Chem. 2003, 68, 6039-6042; f) M. E. Krafft, Z. Fu, L. V. R. Boñaga, Tetrahedron Lett. 2001, 42, 1427-1432; for a short review on inter- and intramolecular PKRs of 2 see also: g) A. Goti, F. M. Cordero, A. Brandi, Top. Curr. Chem. 1996, 178, 1-97.
39. Intermolecular PKRs: a) H. Corlay, I.W. James, E. Fouquet, J. Schmidt, W. B. Motherwell, Synlett 1996, 990-992; b) B. Witulski, T. Stengel, Angew. Chem. 1998, 110, 495-498; Angew. Chem. Int. Ed. Engl. 1998, 37, 489-492; intramolecular PKRs: c) S. Bräse, S. Schömenauer, G. McGaffin, A. Stolle, A. de Meijere, Chem. Eur, J. 1996, 2, 545-555; d) H. Corlay, E. Fouquet, E. Magnier, W.B. Motherwell, Chem. Commun. 1999, 183-184; e) M.E. Krafft, L.V.R. Boñaga, A. S. Felts, C. Hirosawa, S. Kerrigan, J. Org. Chem. 2003, 68, 6039-6042; f) M. E. Krafft, Z. Fu, L. V. R. Boñaga, Tetrahedron Lett. 2001, 42, 1427-1432; for a short review on inter- and intramolecular PKRs of 2 see also: g) A. Goti, F. M. Cordero, A. Brandi, Top. Curr. Chem. 1996, 178, 1-97.
40. Intermolecular PKRs: a) H. Corlay, I.W. James, E. Fouquet, J. Schmidt, W. B. Motherwell, Synlett 1996, 990-992; b) B. Witulski, T. Stengel, Angew. Chem. 1998, 110, 495-498; Angew. Chem. Int. Ed. Engl. 1998, 37, 489-492; intramolecular PKRs: c) S. Bräse, S. Schömenauer, G. McGaffin, A. Stolle, A. de Meijere, Chem. Eur, J. 1996, 2, 545-555; d) H. Corlay, E. Fouquet, E. Magnier, W.B. Motherwell, Chem. Commun. 1999, 183-184; e) M.E. Krafft, L.V.R. Boñaga, A. S. Felts, C. Hirosawa, S. Kerrigan, J. Org. Chem. 2003, 68, 6039-6042; f) M. E. Krafft, Z. Fu, L. V. R. Boñaga, Tetrahedron Lett. 2001, 42, 1427-1432; for a short review on inter- and intramolecular PKRs of 2 see also: g) A. Goti, F. M. Cordero, A. Brandi, Top. Curr. Chem. 1996, 178, 1-97.
41. Intermolecular PKRs: a) H. Corlay, I.W. James, E. Fouquet, J. Schmidt, W. B. Motherwell, Synlett 1996, 990-992; b) B. Witulski, T. Stengel, Angew. Chem. 1998, 110, 495-498; Angew. Chem. Int. Ed. Engl. 1998, 37, 489-492; intramolecular PKRs: c) S. Bräse, S. Schömenauer, G. McGaffin, A. Stolle, A. de Meijere, Chem. Eur, J. 1996, 2, 545-555; d) H. Corlay, E. Fouquet, E. Magnier, W.B. Motherwell, Chem. Commun. 1999, 183-184; e) M.E. Krafft, L.V.R. Boñaga, A. S. Felts, C. Hirosawa, S. Kerrigan, J. Org. Chem. 2003, 68, 6039-6042; f) M. E. Krafft, Z. Fu, L. V. R. Boñaga, Tetrahedron Lett. 2001, 42, 1427-1432; for a short review on inter- and intramolecular PKRs of 2 see also: g) A. Goti, F. M. Cordero, A. Brandi, Top. Curr. Chem. 1996, 178, 1-97.
42. Intermolecular PKRs: a) H. Corlay, I.W. James, E. Fouquet, J. Schmidt, W. B. Motherwell, Synlett 1996, 990-992; b) B. Witulski, T. Stengel, Angew. Chem. 1998, 110, 495-498; Angew. Chem. Int. Ed. Engl. 1998, 37, 489-492; intramolecular PKRs: c) S. Bräse, S. Schömenauer, G. McGaffin, A. Stolle, A. de Meijere, Chem. Eur, J. 1996, 2, 545-555; d) H. Corlay, E. Fouquet, E. Magnier, W.B. Motherwell, Chem. Commun. 1999, 183-184; e) M.E. Krafft, L.V.R. Boñaga, A. S. Felts, C. Hirosawa, S. Kerrigan, J. Org. Chem. 2003, 68, 6039-6042; f) M. E. Krafft, Z. Fu, L. V. R. Boñaga, Tetrahedron Lett. 2001, 42, 1427-1432; for a short review on inter- and intramolecular PKRs of 2 see also: g) A. Goti, F. M. Cordero, A. Brandi, Top. Curr. Chem. 1996, 178, 1-97.
43. Intermolecular PKRs: a) H. Corlay, I.W. James, E. Fouquet, J. Schmidt, W. B. Motherwell, Synlett 1996, 990-992; b) B. Witulski, T. Stengel, Angew. Chem. 1998, 110, 495-498; Angew. Chem. Int. Ed. Engl. 1998, 37, 489-492; intramolecular PKRs: c) S. Bräse, S. Schömenauer, G. McGaffin, A. Stolle, A. de Meijere, Chem. Eur, J. 1996, 2, 545-555; d) H. Corlay, E. Fouquet, E. Magnier, W.B. Motherwell, Chem. Commun. 1999, 183-184; e) M.E. Krafft, L.V.R. Boñaga, A. S. Felts, C. Hirosawa, S. Kerrigan, J. Org. Chem. 2003, 68, 6039-6042; f) M. E. Krafft, Z. Fu, L. V. R. Boñaga, Tetrahedron Lett. 2001, 42, 1427-1432; for a short review on inter- and intramolecular PKRs of 2 see also: g) A. Goti, F. M. Cordero, A. Brandi, Top. Curr. Chem. 1996, 178, 1-97.
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73. These values are somewhat lower than those obtained by repetition of our results, but with 2,5-dimethoxy-2,5-dimethylhexane-3,4-diol as an auxiliary, for which diastereoselection in the range of 1:10 to 1:20 has recently been reported; see ret [10e].
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