Pallidium catalysed reactions of allenes, carbon monoxide and nucleophiles

Tetrahedron

Volumn 54, Issue 15, 1998, Pages 3885-3894

  Grigg, Ronald ^b   Monteith, Michael ^a   Sridharan, Visuvanathar ^b   Terrier, Catherine ^b  

^a ASTRAZENECA   (United Kingdom)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACRYLAMIDE DERIVATIVE; ALLENE DERIVATIVE; AMINE; CARBON MONOXIDE; HYDROXYL GROUP; METHACRYLIC ACID METHYL ESTER; OXIME; PALLADIUM; PHENOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DERIVATIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032499065     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00115-X     Document Type: Article

References (41)

1. 1. For intermolecular processes see: Besson, L.; Gore, J.; Cazes, B.; Tetrahedron Lett., 1995, 36, 3853-3856 and 3857-3860; Yamamoto, Y.; Al-Masum, M.; Fujiwara, N.; Chem. Commun., 1996, 381-382; Trost, B.M.; Gerusz, V.J.; J. Am. Chem. Soc., 1995, 117, 5156-5157. Maguro, M.; Kamijo, S.; Yamamoto, Y.; ibid, 1996, 37, 7453-7456.
2. 1. For intermolecular processes see: Besson, L.; Gore, J.; Cazes, B.; Tetrahedron Lett., 1995, 36, 3853-3856 and 3857-3860; Yamamoto, Y.; Al-Masum, M.; Fujiwara, N.; Chem. Commun., 1996, 381-382; Trost, B.M.; Gerusz, V.J.; J. Am. Chem. Soc., 1995, 117, 5156-5157. Maguro, M.; Kamijo, S.; Yamamoto, Y.; ibid, 1996, 37, 7453-7456.
3. 1. For intermolecular processes see: Besson, L.; Gore, J.; Cazes, B.; Tetrahedron Lett., 1995, 36, 3853-3856 and 3857-3860; Yamamoto, Y.; Al-Masum, M.; Fujiwara, N.; Chem. Commun., 1996, 381-382; Trost, B.M.; Gerusz, V.J.; J. Am. Chem. Soc., 1995, 117, 5156-5157. Maguro, M.; Kamijo, S.; Yamamoto, Y.; ibid, 1996, 37, 7453-7456.
4. 1. For intermolecular processes see: Besson, L.; Gore, J.; Cazes, B.; Tetrahedron Lett., 1995, 36, 3853-3856 and 3857-3860; Yamamoto, Y.; Al-Masum, M.; Fujiwara, N.; Chem. Commun., 1996, 381-382; Trost, B.M.; Gerusz, V.J.; J. Am. Chem. Soc., 1995, 117, 5156-5157. Maguro, M.; Kamijo, S.; Yamamoto, Y.; ibid, 1996, 37, 7453-7456.
5. 2. For cyclisation processes see: Grigg, R.; J. Heterocyclic Chem., 1994, 31, 631-639; Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F.; Chem Rev., 1996, 96, 365-393; Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J.; Chem. Rev., 1996, 96, 635-662; Balme, G.; Bouyssi, D.; Tetrahedron, 1994, 50, 403-414; Davies, I.W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87; Walkup, R.D.; Guan, L.F.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808. For cyclisation cascades involving allene/nucleophiles see: Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Savic, V.; Grigg, R.; Sridharan, V.; ibid, 1996, 37, 6565-6568. Grigg, R.; Rasul, R.; Savic, V.; ibid, 1997, 38, 1825-1828.
6. 2. For cyclisation processes see: Grigg, R.; J. Heterocyclic Chem., 1994, 31, 631-639; Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F.; Chem Rev., 1996, 96, 365-393; Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J.; Chem. Rev., 1996, 96, 635-662; Balme, G.; Bouyssi, D.; Tetrahedron, 1994, 50, 403-414; Davies, I.W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87; Walkup, R.D.; Guan, L.F.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808. For cyclisation cascades involving allene/nucleophiles see: Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Savic, V.; Grigg, R.; Sridharan, V.; ibid, 1996, 37, 6565-6568. Grigg, R.; Rasul, R.; Savic, V.; ibid, 1997, 38, 1825-1828.
7. 2. For cyclisation processes see: Grigg, R.; J. Heterocyclic Chem., 1994, 31, 631-639; Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F.; Chem Rev., 1996, 96, 365-393; Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J.; Chem. Rev., 1996, 96, 635-662; Balme, G.; Bouyssi, D.; Tetrahedron, 1994, 50, 403-414; Davies, I.W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87; Walkup, R.D.; Guan, L.F.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808. For cyclisation cascades involving allene/nucleophiles see: Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Savic, V.; Grigg, R.; Sridharan, V.; ibid, 1996, 37, 6565-6568. Grigg, R.; Rasul, R.; Savic, V.; ibid, 1997, 38, 1825-1828.
8. 2. For cyclisation processes see: Grigg, R.; J. Heterocyclic Chem., 1994, 31, 631-639; Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F.; Chem Rev., 1996, 96, 365-393; Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J.; Chem. Rev., 1996, 96, 635-662; Balme, G.; Bouyssi, D.; Tetrahedron, 1994, 50, 403-414; Davies, I.W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87; Walkup, R.D.; Guan, L.F.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808. For cyclisation cascades involving allene/nucleophiles see: Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Savic, V.; Grigg, R.; Sridharan, V.; ibid, 1996, 37, 6565-6568. Grigg, R.; Rasul, R.; Savic, V.; ibid, 1997, 38, 1825-1828.
9. 2. For cyclisation processes see: Grigg, R.; J. Heterocyclic Chem., 1994, 31, 631-639; Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F.; Chem Rev., 1996, 96, 365-393; Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J.; Chem. Rev., 1996, 96, 635-662; Balme, G.; Bouyssi, D.; Tetrahedron, 1994, 50, 403-414; Davies, I.W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87; Walkup, R.D.; Guan, L.F.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808. For cyclisation cascades involving allene/nucleophiles see: Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Savic, V.; Grigg, R.; Sridharan, V.; ibid, 1996, 37, 6565-6568. Grigg, R.; Rasul, R.; Savic, V.; ibid, 1997, 38, 1825-1828.
10. 2. For cyclisation processes see: Grigg, R.; J. Heterocyclic Chem., 1994, 31, 631-639; Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F.; Chem Rev., 1996, 96, 365-393; Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J.; Chem. Rev., 1996, 96, 635-662; Balme, G.; Bouyssi, D.; Tetrahedron, 1994, 50, 403-414; Davies, I.W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87; Walkup, R.D.; Guan, L.F.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808. For cyclisation cascades involving allene/nucleophiles see: Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Savic, V.; Grigg, R.; Sridharan, V.; ibid, 1996, 37, 6565-6568. Grigg, R.; Rasul, R.; Savic, V.; ibid, 1997, 38, 1825-1828.
11. 2. For cyclisation processes see: Grigg, R.; J. Heterocyclic Chem., 1994, 31, 631-639; Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F.; Chem Rev., 1996, 96, 365-393; Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J.; Chem. Rev., 1996, 96, 635-662; Balme, G.; Bouyssi, D.; Tetrahedron, 1994, 50, 403-414; Davies, I.W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87; Walkup, R.D.; Guan, L.F.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808. For cyclisation cascades involving allene/nucleophiles see: Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Savic, V.; Grigg, R.; Sridharan, V.; ibid, 1996, 37, 6565-6568. Grigg, R.; Rasul, R.; Savic, V.; ibid, 1997, 38, 1825-1828.
12. 2. For cyclisation processes see: Grigg, R.; J. Heterocyclic Chem., 1994, 31, 631-639; Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F.; Chem Rev., 1996, 96, 365-393; Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J.; Chem. Rev., 1996, 96, 635-662; Balme, G.; Bouyssi, D.; Tetrahedron, 1994, 50, 403-414; Davies, I.W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87; Walkup, R.D.; Guan, L.F.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808. For cyclisation cascades involving allene/nucleophiles see: Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Savic, V.; Grigg, R.; Sridharan, V.; ibid, 1996, 37, 6565-6568. Grigg, R.; Rasul, R.; Savic, V.; ibid, 1997, 38, 1825-1828.
13. 2. For cyclisation processes see: Grigg, R.; J. Heterocyclic Chem., 1994, 31, 631-639; Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F.; Chem Rev., 1996, 96, 365-393; Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R.J.; Chem. Rev., 1996, 96, 635-662; Balme, G.; Bouyssi, D.; Tetrahedron, 1994, 50, 403-414; Davies, I.W.; Scopes, D.I.C.; Gallagher, T., Synlett., 1993, 85-87; Walkup, R.D.; Guan, L.F.; Kim, Y.S.; Kim, S.W.; Tetrahedron Lett., 1995, 36, 3805-3808. For cyclisation cascades involving allene/nucleophiles see: Terrier, C.; Tetrahedron Lett., 1996, 37, 4221-4224; Grigg, R.; Savic, V.; Grigg, R.; Sridharan, V.; ibid, 1996, 37, 6565-6568. Grigg, R.; Rasul, R.; Savic, V.; ibid, 1997, 38, 1825-1828.
14. 3. For cycloaddition processes see: O'Connor, J.M.; Stallman, B.J.; Clark, W.G.; Shu, A.Y.L.; Spada, R.E.; Stevenson, T.M.; Dieck, H.A.; J. Org. Chem., 1983, 48, 807-809; An, Z.W.; Catellani, M.; Chiusoli, GP.; J. Organomet. Chem., 1990, 397, C31-C32; Kalinin, V.N.; Shostakovsky, M.V.; Ponomayov, A.B.; Tetrahedron Lett., 1990, 31, 4073-4076. Larock, R.C.; Zenner, J.M.; J. Org. Chem., 1995, 60, 482-483; Larock, R.C.; Guo, L.Q..; Synlett., 1995, 465-466;
15. 3. For cycloaddition processes see: O'Connor, J.M.; Stallman, B.J.; Clark, W.G.; Shu, A.Y.L.; Spada, R.E.; Stevenson, T.M.; Dieck, H.A.; J. Org. Chem., 1983, 48, 807-809; An, Z.W.; Catellani, M.; Chiusoli, GP.; J. Organomet. Chem., 1990, 397, C31-C32; Kalinin, V.N.; Shostakovsky, M.V.; Ponomayov, A.B.; Tetrahedron Lett., 1990, 31, 4073-4076. Larock, R.C.; Zenner, J.M.; J. Org. Chem., 1995, 60, 482-483; Larock, R.C.; Guo, L.Q..; Synlett., 1995, 465-466;
16. 3. For cycloaddition processes see: O'Connor, J.M.; Stallman, B.J.; Clark, W.G.; Shu, A.Y.L.; Spada, R.E.; Stevenson, T.M.; Dieck, H.A.; J. Org. Chem., 1983, 48, 807-809; An, Z.W.; Catellani, M.; Chiusoli, GP.; J. Organomet. Chem., 1990, 397, C31-C32; Kalinin, V.N.; Shostakovsky, M.V.; Ponomayov, A.B.; Tetrahedron Lett., 1990, 31, 4073-4076. Larock, R.C.; Zenner, J.M.; J. Org. Chem., 1995, 60, 482-483; Larock, R.C.; Guo, L.Q..; Synlett., 1995, 465-466;
17. 3. For cycloaddition processes see: O'Connor, J.M.; Stallman, B.J.; Clark, W.G.; Shu, A.Y.L.; Spada, R.E.; Stevenson, T.M.; Dieck, H.A.; J. Org. Chem., 1983, 48, 807-809; An, Z.W.; Catellani, M.; Chiusoli, GP.; J. Organomet. Chem., 1990, 397, C31-C32; Kalinin, V.N.; Shostakovsky, M.V.; Ponomayov, A.B.; Tetrahedron Lett., 1990, 31, 4073-4076. Larock, R.C.; Zenner, J.M.; J. Org. Chem., 1995, 60, 482-483; Larock, R.C.; Guo, L.Q..; Synlett., 1995, 465-466;
18. 3. For cycloaddition processes see: O'Connor, J.M.; Stallman, B.J.; Clark, W.G.; Shu, A.Y.L.; Spada, R.E.; Stevenson, T.M.; Dieck, H.A.; J. Org. Chem., 1983, 48, 807-809; An, Z.W.; Catellani, M.; Chiusoli, GP.; J. Organomet. Chem., 1990, 397, C31-C32; Kalinin, V.N.; Shostakovsky, M.V.; Ponomayov, A.B.; Tetrahedron Lett., 1990, 31, 4073-4076. Larock, R.C.; Zenner, J.M.; J. Org. Chem., 1995, 60, 482-483; Larock, R.C.; Guo, L.Q..; Synlett., 1995, 465-466;
19. Chen, C.-Y.; Lieberman, D.R.; Larsen, R.D.; Reamer, R.A.; Verhoeven, T.R.; Reider, P.J.; Cottrell, I.F.; Houghton, P.G.; Tetrahedron Lett., 1994, 35, 6981-6984;
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24. 5. Grigg, R.; Brown, S.; Sridharan, V.; Uttley, M.D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R.; ibid, 1997, 38,4489-4492; Okuro, K.; Alper, H.; J. Org. Chem., 1997, 62, 1566-1567.
25. 5. Grigg, R.; Brown, S.; Sridharan, V.; Uttley, M.D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R.; ibid, 1997, 38,4489-4492; Okuro, K.; Alper, H.; J. Org. Chem., 1997, 62, 1566-1567.
26. 5. Grigg, R.; Brown, S.; Sridharan, V.; Uttley, M.D., Tetrahedron Lett., 1997, 38, 5031-5034; Grigg, R.; Pratt, R.; ibid, 1997, 38,4489-4492; Okuro, K.; Alper, H.; J. Org. Chem., 1997, 62, 1566-1567.
27. 6. The normal regiochemistry can be perturbed by adverse steric factors e.g. see: Grigg, R.; Rasul, R.; Redpath, J.; Sridharan, V.; Wilson, D., Tetrahedron Lett., 1996, 37, 4609-4612; Oppolzer, W.; Pimm, A.; Stammen. B and Hume, W.E., Helv. Chim. Acta., 1997, 80, 623-639. For an alternative strategy for perturbing regiochemistry see: Grigg, R.; Sansano, J.M.; Tetrahedron, 1996, 52, 13441-13454.
28. 6. The normal regiochemistry can be perturbed by adverse steric factors e.g. see: Grigg, R.; Rasul, R.; Redpath, J.; Sridharan, V.; Wilson, D., Tetrahedron Lett., 1996, 37, 4609-4612; Oppolzer, W.; Pimm, A.; Stammen. B and Hume, W.E., Helv. Chim. Acta., 1997, 80, 623-639. For an alternative strategy for perturbing regiochemistry see: Grigg, R.; Sansano, J.M.; Tetrahedron, 1996, 52, 13441-13454.
29. 6. The normal regiochemistry can be perturbed by adverse steric factors e.g. see: Grigg, R.; Rasul, R.; Redpath, J.; Sridharan, V.; Wilson, D., Tetrahedron Lett., 1996, 37, 4609-4612; Oppolzer, W.; Pimm, A.; Stammen. B and Hume, W.E., Helv. Chim. Acta., 1997, 80, 623-639. For an alternative strategy for perturbing regiochemistry see: Grigg, R.; Sansano, J.M.; Tetrahedron, 1996, 52, 13441-13454.
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