Unexpected regiocontrol in the Pauson-Khand reaction due to 2-furyl substitution of the alkene component

Chemical Communications

Volumn , Issue 17, 1997, Pages 1627-1628

  Harwood, Laurence M ^a   Tejera, Lucía San Andrés ^b,c  

^a UNIVERSITY OF READING   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344372611     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a703786d     Document Type: Article

References (27)

1. For reviews, see N. E. Schore, Org. React., 1991, 40, 1; N. E. Schore, Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, Oxford, 1991, vol. 5, pp. 1037-1064; P. L. Pauson, Tetrahedron, 1985, 41, 5855.
2. For reviews, see N. E. Schore, Org. React., 1991, 40, 1; N. E. Schore, Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, Oxford, 1991, vol. 5, pp. 1037-1064; P. L. Pauson, Tetrahedron, 1985, 41, 5855.
3. For reviews, see N. E. Schore, Org. React., 1991, 40, 1; N. E. Schore, Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, Oxford, 1991, vol. 5, pp. 1037-1064; P. L. Pauson, Tetrahedron, 1985, 41, 5855.
4. For examples of chiral substrates, see C. Almansa, A. Moyano and F. Serratosa, Tetrahedron, 1988, 44, 2657; S. Takano, K. Inomato and K. Ogasawana, J. Chem. Soc., Chem. Commun., 1992, 169; C. Johnstone, W. J. Kerr and U. Lange, J. Chem. Soc., Chem. Commun., 1995, 457; C. Mukai, M. Uchiyama, S. Sakamoto and M. Hanaoka, Tetrahedron Lett. 1995, 36, 5761; H. B. Park, B. Y. Lee, Y. K. Cheng and Y. K. Chung, Organometallics, 1995, 14, 3104; J. Tormo, X. Verdaguer, A. Moyano, M. A. Pericàs and A. Riera, Tetrahedron, 1996, 52, 14021. Chiral amine oxide promoted reaction: W. J. Kerr, G. G. Kirk and D. Middlemiss, Synlett, 1995, 1085. Chirally modified alkyne-cobalt complex: A. M. Hay, W. J. Kerr, G. G. Kirk and D. Middlemiss, Organometallics, 1995, 14, 4986.
5. For examples of chiral substrates, see C. Almansa, A. Moyano and F. Serratosa, Tetrahedron, 1988, 44, 2657; S. Takano, K. Inomato and K. Ogasawana, J. Chem. Soc., Chem. Commun., 1992, 169; C. Johnstone, W. J. Kerr and U. Lange, J. Chem. Soc., Chem. Commun., 1995, 457; C. Mukai, M. Uchiyama, S. Sakamoto and M. Hanaoka, Tetrahedron Lett. 1995, 36, 5761; H. B. Park, B. Y. Lee, Y. K. Cheng and Y. K. Chung, Organometallics, 1995, 14, 3104; J. Tormo, X. Verdaguer, A. Moyano, M. A. Pericàs and A. Riera, Tetrahedron, 1996, 52, 14021. Chiral amine oxide promoted reaction: W. J. Kerr, G. G. Kirk and D. Middlemiss, Synlett, 1995, 1085. Chirally modified alkyne-cobalt complex: A. M. Hay, W. J. Kerr, G. G. Kirk and D. Middlemiss, Organometallics, 1995, 14, 4986.
6. For examples of chiral substrates, see C. Almansa, A. Moyano and F. Serratosa, Tetrahedron, 1988, 44, 2657; S. Takano, K. Inomato and K. Ogasawana, J. Chem. Soc., Chem. Commun., 1992, 169; C. Johnstone, W. J. Kerr and U. Lange, J. Chem. Soc., Chem. Commun., 1995, 457; C. Mukai, M. Uchiyama, S. Sakamoto and M. Hanaoka, Tetrahedron Lett. 1995, 36, 5761; H. B. Park, B. Y. Lee, Y. K. Cheng and Y. K. Chung, Organometallics, 1995, 14, 3104; J. Tormo, X. Verdaguer, A. Moyano, M. A. Pericàs and A. Riera, Tetrahedron, 1996, 52, 14021. Chiral amine oxide promoted reaction: W. J. Kerr, G. G. Kirk and D. Middlemiss, Synlett, 1995, 1085. Chirally modified alkyne-cobalt complex: A. M. Hay, W. J. Kerr, G. G. Kirk and D. Middlemiss, Organometallics, 1995, 14, 4986.
7. For examples of chiral substrates, see C. Almansa, A. Moyano and F. Serratosa, Tetrahedron, 1988, 44, 2657; S. Takano, K. Inomato and K. Ogasawana, J. Chem. Soc., Chem. Commun., 1992, 169; C. Johnstone, W. J. Kerr and U. Lange, J. Chem. Soc., Chem. Commun., 1995, 457; C. Mukai, M. Uchiyama, S. Sakamoto and M. Hanaoka, Tetrahedron Lett. 1995, 36, 5761; H. B. Park, B. Y. Lee, Y. K. Cheng and Y. K. Chung, Organometallics, 1995, 14, 3104; J. Tormo, X. Verdaguer, A. Moyano, M. A. Pericàs and A. Riera, Tetrahedron, 1996, 52, 14021. Chiral amine oxide promoted reaction: W. J. Kerr, G. G. Kirk and D. Middlemiss, Synlett, 1995, 1085. Chirally modified alkyne-cobalt complex: A. M. Hay, W. J. Kerr, G. G. Kirk and D. Middlemiss, Organometallics, 1995, 14, 4986.
8. For examples of chiral substrates, see C. Almansa, A. Moyano and F. Serratosa, Tetrahedron, 1988, 44, 2657; S. Takano, K. Inomato and K. Ogasawana, J. Chem. Soc., Chem. Commun., 1992, 169; C. Johnstone, W. J. Kerr and U. Lange, J. Chem. Soc., Chem. Commun., 1995, 457; C. Mukai, M. Uchiyama, S. Sakamoto and M. Hanaoka, Tetrahedron Lett. 1995, 36, 5761; H. B. Park, B. Y. Lee, Y. K. Cheng and Y. K. Chung, Organometallics, 1995, 14, 3104; J. Tormo, X. Verdaguer, A. Moyano, M. A. Pericàs and A. Riera, Tetrahedron, 1996, 52, 14021. Chiral amine oxide promoted reaction: W. J. Kerr, G. G. Kirk and D. Middlemiss, Synlett, 1995, 1085. Chirally modified alkyne-cobalt complex: A. M. Hay, W. J. Kerr, G. G. Kirk and D. Middlemiss, Organometallics, 1995, 14, 4986.
9. For examples of chiral substrates, see C. Almansa, A. Moyano and F. Serratosa, Tetrahedron, 1988, 44, 2657; S. Takano, K. Inomato and K. Ogasawana, J. Chem. Soc., Chem. Commun., 1992, 169; C. Johnstone, W. J. Kerr and U. Lange, J. Chem. Soc., Chem. Commun., 1995, 457; C. Mukai, M. Uchiyama, S. Sakamoto and M. Hanaoka, Tetrahedron Lett. 1995, 36, 5761; H. B. Park, B. Y. Lee, Y. K. Cheng and Y. K. Chung, Organometallics, 1995, 14, 3104; J. Tormo, X. Verdaguer, A. Moyano, M. A. Pericàs and A. Riera, Tetrahedron, 1996, 52, 14021. Chiral amine oxide promoted reaction: W. J. Kerr, G. G. Kirk and D. Middlemiss, Synlett, 1995, 1085. Chirally modified alkyne-cobalt complex: A. M. Hay, W. J. Kerr, G. G. Kirk and D. Middlemiss, Organometallics, 1995, 14, 4986.
10. For examples of chiral substrates, see C. Almansa, A. Moyano and F. Serratosa, Tetrahedron, 1988, 44, 2657; S. Takano, K. Inomato and K. Ogasawana, J. Chem. Soc., Chem. Commun., 1992, 169; C. Johnstone, W. J. Kerr and U. Lange, J. Chem. Soc., Chem. Commun., 1995, 457; C. Mukai, M. Uchiyama, S. Sakamoto and M. Hanaoka, Tetrahedron Lett. 1995, 36, 5761; H. B. Park, B. Y. Lee, Y. K. Cheng and Y. K. Chung, Organometallics, 1995, 14, 3104; J. Tormo, X. Verdaguer, A. Moyano, M. A. Pericàs and A. Riera, Tetrahedron, 1996, 52, 14021. Chiral amine oxide promoted reaction: W. J. Kerr, G. G. Kirk and D. Middlemiss, Synlett, 1995, 1085. Chirally modified alkyne-cobalt complex: A. M. Hay, W. J. Kerr, G. G. Kirk and D. Middlemiss, Organometallics, 1995, 14, 4986.
11. For examples of chiral substrates, see C. Almansa, A. Moyano and F. Serratosa, Tetrahedron, 1988, 44, 2657; S. Takano, K. Inomato and K. Ogasawana, J. Chem. Soc., Chem. Commun., 1992, 169; C. Johnstone, W. J. Kerr and U. Lange, J. Chem. Soc., Chem. Commun., 1995, 457; C. Mukai, M. Uchiyama, S. Sakamoto and M. Hanaoka, Tetrahedron Lett. 1995, 36, 5761; H. B. Park, B. Y. Lee, Y. K. Cheng and Y. K. Chung, Organometallics, 1995, 14, 3104; J. Tormo, X. Verdaguer, A. Moyano, M. A. Pericàs and A. Riera, Tetrahedron, 1996, 52, 14021. Chiral amine oxide promoted reaction: W. J. Kerr, G. G. Kirk and D. Middlemiss, Synlett, 1995, 1085. Chirally modified alkyne-cobalt complex: A. M. Hay, W. J. Kerr, G. G. Kirk and D. Middlemiss, Organometallics, 1995, 14, 4986.
12. S. Shambayati, W. E. Crowe and S. L. Schreiber, Tetrahedron Lett., 1990, 31, 5289; N. Jeong, Y. K. Chung, B. Lee, H. L. Lee and S-E. Yoo, Synlett, 1991, 204; A. R. Gordon, C. Johnstone and W. J. Kerr, Synlett, 1995, 1083; J. G. Donkervoort, A. R. Gordon, C. Johnstone, W. J. Kerr and U. Lange, Tetrahedron, 1996, 52, 7391.
13. S. Shambayati, W. E. Crowe and S. L. Schreiber, Tetrahedron Lett., 1990, 31, 5289; N. Jeong, Y. K. Chung, B. Lee, H. L. Lee and S-E. Yoo, Synlett, 1991, 204; A. R. Gordon, C. Johnstone and W. J. Kerr, Synlett, 1995, 1083; J. G. Donkervoort, A. R. Gordon, C. Johnstone, W. J. Kerr and U. Lange, Tetrahedron, 1996, 52, 7391.
14. S. Shambayati, W. E. Crowe and S. L. Schreiber, Tetrahedron Lett., 1990, 31, 5289; N. Jeong, Y. K. Chung, B. Lee, H. L. Lee and S-E. Yoo, Synlett, 1991, 204; A. R. Gordon, C. Johnstone and W. J. Kerr, Synlett, 1995, 1083; J. G. Donkervoort, A. R. Gordon, C. Johnstone, W. J. Kerr and U. Lange, Tetrahedron, 1996, 52, 7391.
15. S. Shambayati, W. E. Crowe and S. L. Schreiber, Tetrahedron Lett., 1990, 31, 5289; N. Jeong, Y. K. Chung, B. Lee, H. L. Lee and S-E. Yoo, Synlett, 1991, 204; A. R. Gordon, C. Johnstone and W. J. Kerr, Synlett, 1995, 1083; J. G. Donkervoort, A. R. Gordon, C. Johnstone, W. J. Kerr and U. Lange, Tetrahedron, 1996, 52, 7391.
16. Naturally Occurring Phorbol Esters, ed. F. J. Evans, C.R.C. Press, Boca Raton, FL, 1986.
17. L. M. Harwood, T. Ishikawa, H. Philips and D. Watkin, J. Chem. Soc., Chem. Commun., 1991, 527 and references cited therein.
18. M. E. Krafft, R. H. Romero and I. L. Scott, Synlett. 1995, 577.
19. The diene is a common side product in this reaction, resulting from lack of insertion of carbon monoxide. It should be noted that aryl substituents on the alkene exert a similar regiodirecting influence to that observed for the 2-furyl group: I. U. Khand and P. L. Pauson, J. Chem. Soc., Perkin Trans 1, 1976, 30; I. U. Khand and P. L. Pauson, J. Chem. Res., 1977, (S) 9; (M) 168; I. U. Khand, E. Murphy and P. L. Pauson, J. Chem. Res., 1978, (S) 350; (M) 4434; I. U. Khand, C. A. L. Mahaffy and P. L. Pauson, J. Chem. Res., 1978, (S) 352; (M) 4454.
20. The diene is a common side product in this reaction, resulting from lack of insertion of carbon monoxide. It should be noted that aryl substituents on the alkene exert a similar regiodirecting influence to that observed for the 2-furyl group: I. U. Khand and P. L. Pauson, J. Chem. Soc., Perkin Trans 1, 1976, 30; I. U. Khand and P. L. Pauson, J. Chem. Res., 1977, (S) 9; (M) 168; I. U. Khand, E. Murphy and P. L. Pauson, J. Chem. Res., 1978, (S) 350; (M) 4434; I. U. Khand, C. A. L. Mahaffy and P. L. Pauson, J. Chem. Res., 1978, (S) 352; (M) 4454.
21. The diene is a common side product in this reaction, resulting from lack of insertion of carbon monoxide. It should be noted that aryl substituents on the alkene exert a similar regiodirecting influence to that observed for the 2-furyl group: I. U. Khand and P. L. Pauson, J. Chem. Soc., Perkin Trans 1, 1976, 30; I. U. Khand and P. L. Pauson, J. Chem. Res., 1977, (S) 9; (M) 168; I. U. Khand, E. Murphy and P. L. Pauson, J. Chem. Res., 1978, (S) 350; (M) 4434; I. U. Khand, C. A. L. Mahaffy and P. L. Pauson, J. Chem. Res., 1978, (S) 352; (M) 4454.
22. The diene is a common side product in this reaction, resulting from lack of insertion of carbon monoxide. It should be noted that aryl substituents on the alkene exert a similar regiodirecting influence to that observed for the 2-furyl group: I. U. Khand and P. L. Pauson, J. Chem. Soc., Perkin Trans 1, 1976, 30; I. U. Khand and P. L. Pauson, J. Chem. Res., 1977, (S) 9; (M) 168; I. U. Khand, E. Murphy and P. L. Pauson, J. Chem. Res., 1978, (S) 350; (M) 4434; I. U. Khand, C. A. L. Mahaffy and P. L. Pauson, J. Chem. Res., 1978, (S) 352; (M) 4454.
23. M. E. Krafft, J. Am. Chem. Soc., 1988, 110, 968; M. E. Krafft, C. A. Juliano, I. L. Scott, C. Wright and M. D. McEachin, J. Am. Chem. Soc., 1991, 113, 1693; M. E. Krafft, I. L. Scott and R. H. Romero, Tetrahedron Lett.. 1992, 33, 3829.
24. M. E. Krafft, J. Am. Chem. Soc., 1988, 110, 968; M. E. Krafft, C. A. Juliano, I. L. Scott, C. Wright and M. D. McEachin, J. Am. Chem. Soc., 1991, 113, 1693; M. E. Krafft, I. L. Scott and R. H. Romero, Tetrahedron Lett.. 1992, 33, 3829.
25. M. E. Krafft, J. Am. Chem. Soc., 1988, 110, 968; M. E. Krafft, C. A. Juliano, I. L. Scott, C. Wright and M. D. McEachin, J. Am. Chem. Soc., 1991, 113, 1693; M. E. Krafft, I. L. Scott and R. H. Romero, Tetrahedron Lett.. 1992, 33, 3829.
26. M.-C. Zaluski, M. Robba and M. Bonhomme, Bull. Soc. Chim. Fr., 1970, 1445.
27. Others have also recently reported the use of this tether: A. Stumpf, N. Jeong and H. Sunghee, Synlett. 1997, 205.