Transition metal-catalyzed [5+2] cycloadditions with substituted cyclopropanes: First studies of regio- and stereoselectivity [14]

Journal of the American Chemical Society

Volumn 121, Issue 44, 1999, Pages 10442-10443

  Wender, Paul A ^a   Dyckman, Alaric J ^a   Husfeld, Craig O ^a   Kadereit, Dieter ^a   Love, Jennifer A ^a   Rieck, Heiko ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; METAL;

CATALYSIS; LETTER; STEREOCHEMISTRY;

EID: 0033544372     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992580+     Document Type: Letter

References (23)

1. Representative examples. [4+4]: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4+2]: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
2. Representative examples. [4+4]: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4+2]: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
3. Representative examples. [4+4]: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4+2]: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
4. Representative examples. [4+4]: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4+2]: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
5. Representative examples. [4+4]: Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679. Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089-1094. [4+2]: Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825. Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.
6. For reviews and related work see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130-4135. Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077-10080.
7. For reviews and related work see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130-4135. Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077-10080.
8. For reviews and related work see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130-4135. Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077-10080.
9. For reviews and related work see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130-4135. Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077-10080.
10. For reviews and related work see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130-4135. Jolly, R. S.; Luedtke. G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966. O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077-10080.
11. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721.
12. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220.
13. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998, 54, 7203-7220.
14. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349.
15. (a)Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977.
16. (b) For an isolated example see: Binger, P.; Wedmann, P.; Kozhushkov, S. I.; de Meijere, A. Eur. J. Org. Chem. 1998, 113-119.
17. Most cycloadditions (e.g., the Diels-Alder cycloaddition) whether concerted or stepwise are based on the reaction of two π-components (e.g., diene and dienophile).
18. For brevity, only one mechanistic possibility is presented. An alternative set of mechanistic possibilities can be formulated around the initial formation of metallacyclohexenes followed then by coordination to the tethered alkyne and convergence on the advanced intermediates E and E′ (see ref 6a). While differing in the timing of connections, the issues of regio- and stereoselectivity are treated similarly.
19. A racemic mixture was used in all cases. Only one enantiomer is depicted for simplicity. For preparation of this and other compounds, see Supporting Information.
20. In a representative procedure, to a base-washed, oven-dried Schlenk flask under an argon atmosphere is added tris(triphenylphosphine)rhodium(I) chloride (10 mol %), silver triflate (10 mol %), and distilled, argon-purged PhMe (6 mL). The solution is stirred for 5 min at room temperature, after which yne-vinylcyclopropane 4a (24.1 mg, 0.082 mmol in 2 mL of PhMe) is added and the solution is heated to 110°C for 1 h. After cooling, the reaction mixture is filtered through a plug of alumina and concentrated. Flash column chromatography (silica gel, EtOAc/hexane) gives cycloadduct 5a in 95% yield as a colorless oil.
21. 2.
22. McGaffin, G.; de Meijere, A.; Walsh, R. Chem. Ber. 1991, 939-945. Ryu, I.; Ikura, K.; Tamura, Y.; Maenaka, J.; Ogawa, A.; Sonoda, N. Synlett 1994, 941-942.
23. McGaffin, G.; de Meijere, A.; Walsh, R. Chem. Ber. 1991, 939-945. Ryu, I.; Ikura, K.; Tamura, Y.; Maenaka, J.; Ogawa, A.; Sonoda, N. Synlett 1994, 941-942.