Novel palladium catalyzed formal [3 + 2] cycloaddition via hydrocarbonation reactions of allenes

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 694-695

  Meguro, Masaki ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALLENE DERIVATIVE; CYCLOPENTANE DERIVATIVE; HYDROCARBON; PALLADIUM;

ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS;

EID: 0033524873     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982208x     Document Type: Article

References (32)

1. For reviews: (a) Hudlicky, T.; Price, J. D. Chem. Rev. 1989, 89, 1467-1486. (b) Krohn, K. In Organic Synthesis Highlights: VCH: Weinheim, 1990; pp 97-104.
2. For reviews: (a) Hudlicky, T.; Price, J. D. Chem. Rev. 1989, 89, 1467- 1486. (b) Krohn, K. In Organic Synthesis Highlights: VCH: Weinheim, 1990; pp 97-104.
3. For reviews: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. (b) Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 271- 314. (c) Binger, P.; Fox, D. In Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; vol. E21c, pp 2997-3059.
4. For reviews: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. (b) Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 271-314. (c) Binger, P.; Fox, D. In Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; vol. E21c, pp 2997-3059.
5. For reviews: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. (b) Chan, D. M. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 271- 314. (c) Binger, P.; Fox, D. In Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; vol. E21c, pp 2997-3059.
6. (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20.
7. (b) Trost, B. M. Pure Appl. Chem. 1988, 60, 1615-1626.
8. Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett. 1985, 26, 3825-3828.
9. (a) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780-5781.
10. (b) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77-151 and references therein.
11. (c) Yamago, S.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1988, 1112-1113.
12. (d) Lautens, M.; Ren, Y.; Delanghe, P. H. M. J. Am. Chem. Soc. 1994, 116, 8821-8822.
13. (e) Corlay, H.; Lewis, R. T.; Motherwell, W. B.; Shipman, M. Tetrahedron 1995, 51, 3303-3318.
14. (a) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019-6020.
15. (b) Yamamoto, Y. Pure Appl. Chem. 1996, 68, 9-14.
16. (c) Yamamoto, Y.; Al-Masum, M.; Fujiwara, N.; Asao, N. Tetrahedron Lett. 1995, 36, 2811-2814.
17. (d) Yamamoto, Y.; Al-Masum, M. Synlett 1995, 969-970.
18. (e) Yamamoto, Y.; Al-Masum, M.; Fujiwara, N. Chem. Commun. 1996, 381-382.
19. (f) Yamamoto, Y.; Al-Masum, M.; Takeda, A. Chem. Commun. 1996, 831-832.
20. See the Supporting Information. The cis stereoselectivities in entries 4-6 (Table 1) were significantly high. The reason for this high cis selectivity is not known at present.
21. The stereochemistries of the diastereomers were not assigned. Balme's group also observed similar phenomena in their reactions. See: Marat, X.; Monteiro, N.; Balme, G. Synlett 1997, 845-847.
22. For recent examples of transition metal catalyzed Michael additions, see: (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc 1989, 111, 5954-5955. (b) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436-12451 and references therein. (c) Sawamura, M.; Hamashita, H.; Ito, Y. Tetrahedron 1994, 50, 4439-4454. (d) Sawamura, M.; Hamashita, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295-8296. (e) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553-8565. (g) Murahashi, S.-I.; Naota, T. Bull. Chem. Soc. Jpn. 1996, 69, 1805-1824.
23. For recent examples of transition metal catalyzed Michael additions, see: (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc 1989, 111, 5954-5955. (b) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436-12451 and references therein. (c) Sawamura, M.; Hamashita, H.; Ito, Y. Tetrahedron 1994, 50, 4439-4454. (d) Sawamura, M.; Hamashita, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295-8296. (e) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553-8565. (g) Murahashi, S.-I.; Naota, T. Bull. Chem. Soc. Jpn. 1996, 69, 1805-1824.
24. For recent examples of transition metal catalyzed Michael additions, see: (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc 1989, 111, 5954-5955. (b) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436-12451 and references therein. (c) Sawamura, M.; Hamashita, H.; Ito, Y. Tetrahedron 1994, 50, 4439-4454. (d) Sawamura, M.; Hamashita, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295-8296. (e) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553-8565. (g) Murahashi, S.-I.; Naota, T. Bull. Chem. Soc. Jpn. 1996, 69, 1805-1824.
25. For recent examples of transition metal catalyzed Michael additions, see: (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc 1989, 111, 5954-5955. (b) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436-12451 and references therein. (c) Sawamura, M.; Hamashita, H.; Ito, Y. Tetrahedron 1994, 50, 4439-4454. (d) Sawamura, M.; Hamashita, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295-8296. (e) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553-8565. (g) Murahashi, S.-I.; Naota, T. Bull. Chem. Soc. Jpn. 1996, 69, 1805-1824.
26. For recent examples of transition metal catalyzed Michael additions, see: (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc 1989, 111, 5954-5955. (b) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436-12451 and references therein. (c) Sawamura, M.; Hamashita, H.; Ito, Y. Tetrahedron 1994, 50, 4439-4454. (d) Sawamura, M.; Hamashita, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295-8296. (e) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553-8565. (g) Murahashi, S.-I.; Naota, T. Bull. Chem. Soc. Jpn. 1996, 69, 1805-1824.
27. For recent examples of transition metal catalyzed Michael additions, see: (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc 1989, 111, 5954-5955. (b) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436-12451 and references therein. (c) Sawamura, M.; Hamashita, H.; Ito, Y. Tetrahedron 1994, 50, 4439-4454. (d) Sawamura, M.; Hamashita, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295-8296. (e) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553-8565. (g) Murahashi, S.-I.; Naota, T. Bull. Chem. Soc. Jpn. 1996, 69, 1805-1824.
28. For recent examples of transition metal catalyzed Michael additions, see: (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc 1989, 111, 5954-5955. (b) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436-12451 and references therein. (c) Sawamura, M.; Hamashita, H.; Ito, Y. Tetrahedron 1994, 50, 4439-4454. (d) Sawamura, M.; Hamashita, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295-8296. (e) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807-2810. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553-8565. (g) Murahashi, S.-I.; Naota, T. Bull. Chem. Soc. Jpn. 1996, 69, 1805-1824.
29. Trost and Gerusz proposed a hydropalladation mechanism for the palladium catalyzed reactions of allenes with active methylene compounds. See: (a) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156-5157. We also proposed his mechanism for the intramolecular reactions. See also: (b) Meguro, M.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 7453-7456.
30. Trost and Gerusz proposed a hydropalladation mechanism for the palladium catalyzed reactions of allenes with active methylene compounds. See: (a) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156- 5157. We also proposed his mechanism for the intramolecular reactions. See also: (b) Meguro, M.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 7453-7456.
31. Without palladium catalysts, the reactions of 4 and 5 did not proceed at all.
32. We could not isolate the Michael addition product in the case of the reactions with 5.