W(CO)5(L)-catalyzed endo-selective cyclization of allenyl silyl enol ethers: An efficient method for the cyclopentene annulation onto α,β-unsaturated ketones

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1725-1728

  Miura, Tomoya ^a   Kiyota, Koichi ^a   Kusama, Hiroyuki ^a   Lee, Kooyeon ^b   Kim, Hyunseok ^b   Kim, Sunggak ^c   Lee, Phil Ho ^b   Iwasawa, Nobuharu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b Kangwon National University   (South Korea)

^c Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYCLOPENTENE DERIVATIVE; DIMETHYL SULFIDE; ETHER DERIVATIVE; INDIUM; KETONE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; TUNGSTEN DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; PRODUCTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 0042851985     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034365a     Document Type: Article

References (24)

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3. For a review on the palladium-catalyzed reaction of allenes, see: Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067-3125.
4. For recent examples of the palladium-catalyzed carbocyclization of allenyl compounds, see: (a) Ma, S.; Zhao, S. Org. Lett. 2000, 2, 2495-2497. (b) Kang, S.-K.; Baik, T.-G.; Kulak, A. N.; Ha, Y.-H.; Lim, Y.; Park, J. J. Am. Chem. Soc. 2000, 122, 11529-11530. (c) Shin, S.; RajanBabu, T. V. J. Am. Chem. Soc. 2001, 123, 8416-8417. (d) Kang, S.-K.; Ha, Y.-H.; Ko, B.-S.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2002, 41, 343-345. (e) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246-11247.
5. For recent examples of the palladium-catalyzed carbocyclization of allenyl compounds, see: (a) Ma, S.; Zhao, S. Org. Lett. 2000, 2, 2495-2497. (b) Kang, S.-K.; Baik, T.-G.; Kulak, A. N.; Ha, Y.-H.; Lim, Y.; Park, J. J. Am. Chem. Soc. 2000, 122, 11529-11530. (c) Shin, S.; RajanBabu, T. V. J. Am. Chem. Soc. 2001, 123, 8416-8417. (d) Kang, S.-K.; Ha, Y.-H.; Ko, B.-S.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2002, 41, 343-345. (e) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246-11247.
6. For recent examples of the palladium-catalyzed carbocyclization of allenyl compounds, see: (a) Ma, S.; Zhao, S. Org. Lett. 2000, 2, 2495-2497. (b) Kang, S.-K.; Baik, T.-G.; Kulak, A. N.; Ha, Y.-H.; Lim, Y.; Park, J. J. Am. Chem. Soc. 2000, 122, 11529-11530. (c) Shin, S.; RajanBabu, T. V. J. Am. Chem. Soc. 2001, 123, 8416-8417. (d) Kang, S.-K.; Ha, Y.-H.; Ko, B.-S.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2002, 41, 343-345. (e) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246-11247.
7. For recent examples of the palladium-catalyzed carbocyclization of allenyl compounds, see: (a) Ma, S.; Zhao, S. Org. Lett. 2000, 2, 2495-2497. (b) Kang, S.-K.; Baik, T.-G.; Kulak, A. N.; Ha, Y.-H.; Lim, Y.; Park, J. J. Am. Chem. Soc. 2000, 122, 11529-11530. (c) Shin, S.; RajanBabu, T. V. J. Am. Chem. Soc. 2001, 123, 8416-8417. (d) Kang, S.-K.; Ha, Y.-H.; Ko, B.-S.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2002, 41, 343-345. (e) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246-11247.
8. For recent examples of the palladium-catalyzed carbocyclization of allenyl compounds, see: (a) Ma, S.; Zhao, S. Org. Lett. 2000, 2, 2495-2497. (b) Kang, S.-K.; Baik, T.-G.; Kulak, A. N.; Ha, Y.-H.; Lim, Y.; Park, J. J. Am. Chem. Soc. 2000, 122, 11529-11530. (c) Shin, S.; RajanBabu, T. V. J. Am. Chem. Soc. 2001, 123, 8416-8417. (d) Kang, S.-K.; Ha, Y.-H.; Ko, B.-S.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2002, 41, 343-345. (e) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246-11247.
9. For a review on the transition-metal catalyzed nucleophilic cyclization of allenyl compounds, see: Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12-21.
10. Transition metal-catalyzed cyclizations of allenyl compounds by heteronucleophiles have been reported. For recent examples of 5-endo-selective cyclization by oxygen nucleophiles, see: (a) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288. (b) Hoffmann-Röder, A.; Krause, N. Org. Lett. 2001, 3, 2537-2538. (c) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2002, 41, 1775-1778.
11. Transition metal-catalyzed cyclizations of allenyl compounds by heteronucleophiles have been reported. For recent examples of 5-endo-selective cyclization by oxygen nucleophiles, see: (a) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288. (b) Hoffmann-Röder, A.; Krause, N. Org. Lett. 2001, 3, 2537-2538. (c) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2002, 41, 1775-1778.
12. Transition metal-catalyzed cyclizations of allenyl compounds by heteronucleophiles have been reported. For recent examples of 5-endo-selective cyclization by oxygen nucleophiles, see: (a) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288. (b) Hoffmann-Röder, A.; Krause, N. Org. Lett. 2001, 3, 2537-2538. (c) Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2002, 41, 1775-1778.
13. For recent examples of 5-endo-selective cyclization by nitrogen nucleophiles, see: (a) Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Osawa, E.; Yamaoka, Y.; Fujii, N.; Ibuka, T. J. Org. Chem. 1999, 64, 2992-2993. (b) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717-720.
14. For recent examples of 5-endo-selective cyclization by nitrogen nucleophiles, see: (a) Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Osawa, E.; Yamaoka, Y.; Fujii, N.; Ibuka, T. J. Org. Chem. 1999, 64, 2992-2993. (b) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717-720.
15. Iwasawa, N.; Miura, T.; Kiyota, K.; Kusama, H.; Lee, K.; Lee, P. H. Org. Lett. 2002, 4, 4463-4466.
16. For another example of 1,4-addition with indium reagents in the presence of t-butyldimethylsilyl triflate and dimethyl sulfide, see: Lee, P. H.; Lee, K. ; Kim, S. Org. Lett. 2001, 3, 3205-3207.
17. For an example of In-mediated propargylation or allenylation, see: (a) Isaac, M. B.; Chan, T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003-1004. (b) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C.-J. J. Org. Chem. 1998, 63, 7472-7480. (c) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453-9459. (d) Lee, K.; Seomoon, D.; Lee, P. H. Angew. Chem., Int. Ed. 2002, 41, 3901-3903.
18. For an example of In-mediated propargylation or allenylation, see: (a) Isaac, M. B.; Chan, T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003-1004. (b) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C.-J. J. Org. Chem. 1998, 63, 7472-7480. (c) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453-9459. (d) Lee, K.; Seomoon, D.; Lee, P. H. Angew. Chem., Int. Ed. 2002, 41, 3901-3903.
19. For an example of In-mediated propargylation or allenylation, see: (a) Isaac, M. B.; Chan, T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003-1004. (b) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C.-J. J. Org. Chem. 1998, 63, 7472-7480. (c) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453-9459. (d) Lee, K.; Seomoon, D.; Lee, P. H. Angew. Chem., Int. Ed. 2002, 41, 3901-3903.
20. For an example of In-mediated propargylation or allenylation, see: (a) Isaac, M. B.; Chan, T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003-1004. (b) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C.-J. J. Org. Chem. 1998, 63, 7472-7480. (c) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453-9459. (d) Lee, K.; Seomoon, D.; Lee, P. H. Angew. Chem., Int. Ed. 2002, 41, 3901-3903.
21. 5(L) complex; see: Kirtley, S. W. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds; Pergamon Press: Oxford, UK, 1982; Vol. 3, pp 1079-1148.
22. 2 was employed, a low yield of 3a was obtained along with a complex mixture of unidentified products.
23. 2O; see: Barluenga, J.; Ballesteros, A.; Rúa, R. B.; Santamaría, J.; Rubio, E.; Tomás, M. J. Am. Chem. Soc. 2003, 125, 1834-1842.
24. While 3a was obtained as a single product, 5 was accompanied by a small amount (about 10% of the product) of the olefinic regioisomer 3a. The reason for the formation of this compound is not yet obvious.