Hydroformylation of ω-functionalized 1,1-disubstituted alkenes and its use toward the synthesis of (±)muscone

Chemistry Letters

Volumn , Issue 12, 1997, Pages 1291-1292

  Takahashi, Takashi ^a   Machida, Kazuhiro ^a   Kido, Yoichi ^a   Nagashima, Kensuke ^a   Ebata, Satoshi ^a   Doi, Takayuki ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002625378     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.1291     Document Type: Article

References (26)

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3. G. D. Cuny and S. L. Buchwald, J. Am. Chem. Soc., 115, 2066 (1993); For review, C. Botteghi, R. Ganzerla, M. Lenarda, and G. Moretti, J. Mol. Cat., 40, 129 (1987).
4. C. K. Brown and G. Wilkinson, J. Chem. Soc., A, 1970, 2753.
5. Phosphite-modified rhodium-catalyzed hydroformylation of less reactive olefins under mild conditions was reported, P. W. N. M. Van Leeuwen and C. F. Roobeek, J. Organomet. Chem., 258, 343 (1983).
6. For examples of the hydroformylation of 1,1-disubstituted alkenes, see: (a) C. K. Brown and G. Wilkinson, J. Chem. Soc., A, 1970, 2753;
7. (b) C. Botteghi, G. Consiglio, G. Ceccarelli, and A. Stefani, J. Org. Chem., 37, 1835 (1972);
8. (c) C. Botteghi, L. Lardicci, and R. Menicagli, J. Org. Chem., 28, 2361 (1973);
9. (d) W. Hoffmann and H. Siegel, Tetrahedron Lett., 1975, 533; Opposite regioselectivity, see:
10. (e) L. Kollár, G. Consiglio, and P. Pino, Chimia, 40, 428 (1986);
11. (f) S. Gladiali and L. Pinna, Tetrahedron: Asymmetry, 2, 623 (1991).
12. For recent examples of diastereoselective hydroformylation of 1,1-disubstituted alkenes: see, T. Doi, H. Komatsu, K. Yamamoto, Tetrahedron Lett., 37, 6877 (1996); B. Breit, Angew. Chem. Int., Ed. Engl., 35, 2835 (1996); B. Breit, Chem. Commun., 1997, 591.
13. For recent examples of diastereoselective hydroformylation of 1,1-disubstituted alkenes: see, T. Doi, H. Komatsu, K. Yamamoto, Tetrahedron Lett., 37, 6877 (1996); B. Breit, Angew. Chem. Int., Ed. Engl., 35, 2835 (1996); B. Breit, Chem. Commun., 1997, 591.
14. For recent examples of diastereoselective hydroformylation of 1,1-disubstituted alkenes: see, T. Doi, H. Komatsu, K. Yamamoto, Tetrahedron Lett., 37, 6877 (1996); B. Breit, Angew. Chem. Int., Ed. Engl., 35, 2835 (1996); B. Breit, Chem. Commun., 1997, 591.
15. For examples of conjugate addition of organocuprates to α,β-unsaturated aldehydes: see, J. A. Kozlowski, in "Comprehensive Organic Synthesis," ed by B. M. Trost, I. Fleming, and M. F. Semmelhack, Pergamon Press, Oxford (1991), Vol. 4, p 183-184.
16. For isolation: see, H. Walbaum, J. Prakt. Chem. II 1906, 73, 488.
17. For recent synthetic works on muscone: see, R. Ballini, E. Marcantoni, and M. Petrini, Liebigs Ann., 1995, 1381; W. Oppolzer and R. N. Radinov, J. Am. Chem. Soc., 115, 1593 (1993); T. Takahashi, H. Yamada, T. Haino, Y. Kido, and Y. Fukazawa, Tetrahedron Lett., 33, 7561 (1992), and references cited therein; T. Ogawa, C.-L. Fang, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1991, 1438; K. Tanaka, H. Ushio, Y. Kawabata, and H. Suzuki, J. Chem. Soc., Perkin Trans. I, 1991, 1445.
18. For recent synthetic works on muscone: see, R. Ballini, E. Marcantoni, and M. Petrini, Liebigs Ann., 1995, 1381; W. Oppolzer and R. N. Radinov, J. Am. Chem. Soc., 115, 1593 (1993); T. Takahashi, H. Yamada, T. Haino, Y. Kido, and Y. Fukazawa, Tetrahedron Lett., 33, 7561 (1992), and references cited therein; T. Ogawa, C.-L. Fang, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1991, 1438; K. Tanaka, H. Ushio, Y. Kawabata, and H. Suzuki, J. Chem. Soc., Perkin Trans. I, 1991, 1445.
19. For recent synthetic works on muscone: see, R. Ballini, E. Marcantoni, and M. Petrini, Liebigs Ann., 1995, 1381; W. Oppolzer and R. N. Radinov, J. Am. Chem. Soc., 115, 1593 (1993); T. Takahashi, H. Yamada, T. Haino, Y. Kido, and Y. Fukazawa, Tetrahedron Lett., 33, 7561 (1992), and references cited therein; T. Ogawa, C.-L. Fang, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1991, 1438; K. Tanaka, H. Ushio, Y. Kawabata, and H. Suzuki, J. Chem. Soc., Perkin Trans. I, 1991, 1445.
20. For recent synthetic works on muscone: see, R. Ballini, E. Marcantoni, and M. Petrini, Liebigs Ann., 1995, 1381; W. Oppolzer and R. N. Radinov, J. Am. Chem. Soc., 115, 1593 (1993); T. Takahashi, H. Yamada, T. Haino, Y. Kido, and Y. Fukazawa, Tetrahedron Lett., 33, 7561 (1992), and references cited therein; T. Ogawa, C.-L. Fang, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1991, 1438; K. Tanaka, H. Ushio, Y. Kawabata, and H. Suzuki, J. Chem. Soc., Perkin Trans. I, 1991, 1445.
21. For recent synthetic works on muscone: see, R. Ballini, E. Marcantoni, and M. Petrini, Liebigs Ann., 1995, 1381; W. Oppolzer and R. N. Radinov, J. Am. Chem. Soc., 115, 1593 (1993); T. Takahashi, H. Yamada, T. Haino, Y. Kido, and Y. Fukazawa, Tetrahedron Lett., 33, 7561 (1992), and references cited therein; T. Ogawa, C.-L. Fang, H. Suemune, and K. Sakai, J. Chem. Soc., Chem. Commun., 1991, 1438; K. Tanaka, H. Ushio, Y. Kawabata, and H. Suzuki, J. Chem. Soc., Perkin Trans. I, 1991, 1445.
22. 3 was used as a catalyst.
23. The hydroformylation of the acetals of the 2-substituted α,β-unsaturated aldehydes in the presence of rhodium catalysts was reported in ref 5c.
24. For intramolecular alkylation of cyanohydrin ethers: see, T. Takahashi, H. Nemoto, and J. Tsuji, Tetrahedron Lett., 24, 2005 (1983); T. Takahashi, T. Nagashima, and J. Tsuji, Tetrahedron Lett., 22, 1359 (1981); G. Stork, J. C. Depezay, and J. d'Angelo, Tetrahedron Lett., 1975, 389.
25. For intramolecular alkylation of cyanohydrin ethers: see, T. Takahashi, H. Nemoto, and J. Tsuji, Tetrahedron Lett., 24, 2005 (1983); T. Takahashi, T. Nagashima, and J. Tsuji, Tetrahedron Lett., 22, 1359 (1981); G. Stork, J. C. Depezay, and J. d'Angelo, Tetrahedron Lett., 1975, 389.
26. For intramolecular alkylation of cyanohydrin ethers: see, T. Takahashi, H. Nemoto, and J. Tsuji, Tetrahedron Lett., 24, 2005 (1983); T. Takahashi, T. Nagashima, and J. Tsuji, Tetrahedron Lett., 22, 1359 (1981); G. Stork, J. C. Depezay, and J. d'Angelo, Tetrahedron Lett., 1975, 389.