Cyclopentenones from carbonylative cycloaddition of Mackenzie's allyl nickel complexes and acetylenes [12]

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 878-879

  García Gómez, Gabriel ^a   Moretó, Josep M ^a  

^a CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CYCLOPENTENONE; NICKEL;

CYCLIZATION; ENZYME KINETICS; LETTER; METAL BINDING; MOLECULAR INTERACTION; REACTION ANALYSIS; SOLVATION; STEREOCHEMISTRY;

EID: 0033518587     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982207m     Document Type: Letter

References (19)

1. See leading references on the Pauson Khand cycloaddition in: (a) Schore, N. E. Comprehensive Organometallic Chemistry II, Abel, E. W., Stone, F. G., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, p 703. (b) Schore, N. E. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037.
2. See leading references on the Pauson Khand cycloaddition in: (a) Schore, N. E. Comprehensive Organometallic Chemistry II, Abel, E. W., Stone, F. G., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, p 703. (b) Schore, N. E. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1037.
3. (a) Chiusoli, G. P.; Cassar, L. Angew. Chem., Int. Ed. Engl. 1967, 6, 124.
4. (b) Camps, F.; Coll, J.; Moretó, J. M.; Torras, J. J. Org. Chem. 1989, 54, 1969-1978.
5. (c) Camps, F.; Moretó, J. M.; Pagès,- Ll. Tetrahedron 1992, 48, 3147-3162.
6. (d) Pagès, Ll.; Llebaria, A.; Camps, F.; Molins, E.; Miravitlles, C.; Moretó, J. M. J. Am. Chem. Soc. 1992, 114, 10449-10461.
7. (e) Oppolzer, W. Pure Appl. Chem. 1990, 62, 1941-1948 and references therein.
8. 4 in the preparation of cyclopentenones through the initial formation of the π-allyl Ni complex from an allyl halide. This work is in progress.
9. Johnson, J. R.; Tully, P. S.; Mackenzie, P. B.; Sabat, M. J. Am. Chem. Soc. 1991, 113, 6172-6177. Grisso, B. A.; Johnson, J. R.; Mackenzie, P. B. J. Am. Chem. Soc. 1992, 114, 5160-5165.
10. Johnson, J. R.; Tully, P. S.; Mackenzie, P. B.; Sabat, M. J. Am. Chem. Soc. 1991, 113, 6172-6177. Grisso, B. A.; Johnson, J. R.; Mackenzie, P. B. J. Am. Chem. Soc. 1992, 114, 5160-5165.
11. Montgomery, J.; Savchenko, A. V.; Zhao, Y. J. Org. Chem. 1995, 60, 5699-5701. Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996, 118, 2099-2100. Montgomery, J.; Oblinger. E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911-4920. Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065-9066.
12. Montgomery, J.; Savchenko, A. V.; Zhao, Y. J. Org. Chem. 1995, 60, 5699-5701. Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996, 118, 2099-2100. Montgomery, J.; Oblinger. E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911-4920. Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065-9066.
13. Montgomery, J.; Savchenko, A. V.; Zhao, Y. J. Org. Chem. 1995, 60, 5699-5701. Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996, 118, 2099-2100. Montgomery, J.; Oblinger. E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911-4920. Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065-9066.
14. Montgomery, J.; Savchenko, A. V.; Zhao, Y. J. Org. Chem. 1995, 60, 5699-5701. Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996, 118, 2099-2100. Montgomery, J.; Oblinger. E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911-4920. Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065-9066.
15. Polyinsertion is also frequent in the conventional methodology. Sometimes it may be supressed to a large extent by the presence of acetate. See ref 2d. The effect of additives in this reactions or optimization of this precise reaction has not been undertaken.
16. Mutual coupling contants J = 3 Hz and NOE experiments are in agreement with the proposed stereochemistry.
17. Ni(0) species are active catalysts for (carbonylative) oligomerizations of both alkynes and strained olefins, see: P. W. Jolly; G. Wilke. The Organic Chemistry of Nickel; Vol. II Academic Press: New York, 1974; Vol. II, pp 39-54, 94-103, 306-313).
18. Ni(0) species are active catalysts for (carbonylative) oligomerizations of both alkynes and strained olefins, see: P. W. Jolly; G. Wilke. The Organic Chemistry of Nickel; Vol. II Academic Press: New York, 1974; Vol. II, pp 39-54, 94-103, 306-313).
19. 1H NMR spectrum of the product mixture.