Diastereoselective hydroformylation of certain protected allylic alcohols

Tetrahedron Letters

Volumn 37, Issue 38, 1996, Pages 6877-6880

  Doi, Takayuki ^a   Komatsu, Hiroshi ^a   Yamamoto, Keiji ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; CYCLOHEXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030590401     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01502-X     Document Type: Article

References (27)

1. 1. Cornils, B. In New Syntheses with Carbon Monoxide; Fable, J. Ed.; Springer-Verlag: New York, 1980. Tolman, C. A.; Faller, J. In Homogeneous Catalysis with Metal Phosphine Complexes; Pígnolet, L. H. Ed.; Plenum Press: New York, 1983; Chapt. 2. Dickson, R. S. In Homogeneous Catalysis with Compounds of Rhodium and Iridium; Ugo, R.; James B. R. Eds.; D. Reidel Publish Company: Dordrecht, 1985. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Cat. A 1995, 104, 17-85. For a recent review of asymmetric hydroformylation, see: Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485-2506.
2. 1. Cornils, B. In New Syntheses with Carbon Monoxide; Fable, J. Ed.; Springer-Verlag: New York, 1980. Tolman, C. A.; Faller, J. In Homogeneous Catalysis with Metal Phosphine Complexes; Pígnolet, L. H. Ed.; Plenum Press: New York, 1983; Chapt. 2. Dickson, R. S. In Homogeneous Catalysis with Compounds of Rhodium and Iridium; Ugo, R.; James B. R. Eds.; D. Reidel Publish Company: Dordrecht, 1985. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Cat. A 1995, 104, 17-85. For a recent review of asymmetric hydroformylation, see: Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485-2506.
3. 1. Cornils, B. In New Syntheses with Carbon Monoxide; Fable, J. Ed.; Springer-Verlag: New York, 1980. Tolman, C. A.; Faller, J. In Homogeneous Catalysis with Metal Phosphine Complexes; Pígnolet, L. H. Ed.; Plenum Press: New York, 1983; Chapt. 2. Dickson, R. S. In Homogeneous Catalysis with Compounds of Rhodium and Iridium; Ugo, R.; James B. R. Eds.; D. Reidel Publish Company: Dordrecht, 1985. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Cat. A 1995, 104, 17-85. For a recent review of asymmetric hydroformylation, see: Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485-2506.
4. 1. Cornils, B. In New Syntheses with Carbon Monoxide; Fable, J. Ed.; Springer-Verlag: New York, 1980. Tolman, C. A.; Faller, J. In Homogeneous Catalysis with Metal Phosphine Complexes; Pígnolet, L. H. Ed.; Plenum Press: New York, 1983; Chapt. 2. Dickson, R. S. In Homogeneous Catalysis with Compounds of Rhodium and Iridium; Ugo, R.; James B. R. Eds.; D. Reidel Publish Company: Dordrecht, 1985. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Cat. A 1995, 104, 17-85. For a recent review of asymmetric hydroformylation, see: Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485-2506.
5. 1. Cornils, B. In New Syntheses with Carbon Monoxide; Fable, J. Ed.; Springer-Verlag: New York, 1980. Tolman, C. A.; Faller, J. In Homogeneous Catalysis with Metal Phosphine Complexes; Pígnolet, L. H. Ed.; Plenum Press: New York, 1983; Chapt. 2. Dickson, R. S. In Homogeneous Catalysis with Compounds of Rhodium and Iridium; Ugo, R.; James B. R. Eds.; D. Reidel Publish Company: Dordrecht, 1985. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Cat. A 1995, 104, 17-85. For a recent review of asymmetric hydroformylation, see: Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485-2506.
6. 2. For the regiocontrolled hydroformylation of bulky silyl group-substituted (Z)-alkenes, see: (a) Doyle, M. M.; Jackson, W. R.; Perlmutter, P. Tetrahedron Lett. 1989, 30, 233-234.
7. (b) Crudden, C. M.; Alper, H. J. Org. Chem, 1994, 59, 3091-3097.
8. 3. For examples of stereoselectivity in the rhodium-catalyzed hydroformylation, see: Lazzaroni, R.; Pucci, S.; Bertozzi, S.; Pini, D. J. Organomet Chem. 1983, 247, C56-58. Azzaroni, F.; Biscarini, P.; Bordoni, S.; Longoni, G.; Venturini, E. J. Organomet. Chem. 1996, 508, 59-67. For the phosphine-directed hydroformylation, see: Burke, S. D.; Cobb, J. E. Tetrahedron Lett. 1986, 27, 4237-4240. Burke, S. D.; Cobb, J. E.; Takeuchi, K. J. Org. Chem. 1990, 55, 2138-2151. Jackson, W. R.; Perlmutter, P.; Suh, G.-H. J. Chem. Soc., Chem. Commun. 1987, 724-725. Jackson, W. R.; Perlmutter, P.; Tasdelen, E. E. Tetrahedron Lett. 1990, 31, 2461-2462. For the phosphite-directed hydroformylation, see: Jackson, W. R.; Moffat, M. R.; Perlmutter, P.; Tasdelen, E. E. Aust. J. Chem. 1992, 45, 823-834.
9. 3. For examples of stereoselectivity in the rhodium-catalyzed hydroformylation, see: Lazzaroni, R.; Pucci, S.; Bertozzi, S.; Pini, D. J. Organomet Chem. 1983, 247, C56-58. Azzaroni, F.; Biscarini, P.; Bordoni, S.; Longoni, G.; Venturini, E. J. Organomet. Chem. 1996, 508, 59-67. For the phosphine-directed hydroformylation, see: Burke, S. D.; Cobb, J. E. Tetrahedron Lett. 1986, 27, 4237-4240. Burke, S. D.; Cobb, J. E.; Takeuchi, K. J. Org. Chem. 1990, 55, 2138-2151. Jackson, W. R.; Perlmutter, P.; Suh, G.-H. J. Chem. Soc., Chem. Commun. 1987, 724-725. Jackson, W. R.; Perlmutter, P.; Tasdelen, E. E. Tetrahedron Lett. 1990, 31, 2461-2462. For the phosphite-directed hydroformylation, see: Jackson, W. R.; Moffat, M. R.; Perlmutter, P.; Tasdelen, E. E. Aust. J. Chem. 1992, 45, 823-834.
10. 3. For examples of stereoselectivity in the rhodium-catalyzed hydroformylation, see: Lazzaroni, R.; Pucci, S.; Bertozzi, S.; Pini, D. J. Organomet Chem. 1983, 247, C56-58. Azzaroni, F.; Biscarini, P.; Bordoni, S.; Longoni, G.; Venturini, E. J. Organomet. Chem. 1996, 508, 59-67. For the phosphine-directed hydroformylation, see: Burke, S. D.; Cobb, J. E. Tetrahedron Lett. 1986, 27, 4237-4240. Burke, S. D.; Cobb, J. E.; Takeuchi, K. J. Org. Chem. 1990, 55, 2138-2151. Jackson, W. R.; Perlmutter, P.; Suh, G.-H. J. Chem. Soc., Chem. Commun. 1987, 724-725. Jackson, W. R.; Perlmutter, P.; Tasdelen, E. E. Tetrahedron Lett. 1990, 31, 2461-2462. For the phosphite-directed hydroformylation, see: Jackson, W. R.; Moffat, M. R.; Perlmutter, P.; Tasdelen, E. E. Aust. J. Chem. 1992, 45, 823-834.
11. 3. For examples of stereoselectivity in the rhodium-catalyzed hydroformylation, see: Lazzaroni, R.; Pucci, S.; Bertozzi, S.; Pini, D. J. Organomet Chem. 1983, 247, C56-58. Azzaroni, F.; Biscarini, P.; Bordoni, S.; Longoni, G.; Venturini, E. J. Organomet. Chem. 1996, 508, 59-67. For the phosphine-directed hydroformylation, see: Burke, S. D.; Cobb, J. E. Tetrahedron Lett. 1986, 27, 4237-4240. Burke, S. D.; Cobb, J. E.; Takeuchi, K. J. Org. Chem. 1990, 55, 2138-2151. Jackson, W. R.; Perlmutter, P.; Suh, G.-H. J. Chem. Soc., Chem. Commun. 1987, 724-725. Jackson, W. R.; Perlmutter, P.; Tasdelen, E. E. Tetrahedron Lett. 1990, 31, 2461-2462. For the phosphite-directed hydroformylation, see: Jackson, W. R.; Moffat, M. R.; Perlmutter, P.; Tasdelen, E. E. Aust. J. Chem. 1992, 45, 823-834.
12. 3. For examples of stereoselectivity in the rhodium-catalyzed hydroformylation, see: Lazzaroni, R.; Pucci, S.; Bertozzi, S.; Pini, D. J. Organomet Chem. 1983, 247, C56-58. Azzaroni, F.; Biscarini, P.; Bordoni, S.; Longoni, G.; Venturini, E. J. Organomet. Chem. 1996, 508, 59-67. For the phosphine-directed hydroformylation, see: Burke, S. D.; Cobb, J. E. Tetrahedron Lett. 1986, 27, 4237-4240. Burke, S. D.; Cobb, J. E.; Takeuchi, K. J. Org. Chem. 1990, 55, 2138-2151. Jackson, W. R.; Perlmutter, P.; Suh, G.-H. J. Chem. Soc., Chem. Commun. 1987, 724-725. Jackson, W. R.; Perlmutter, P.; Tasdelen, E. E. Tetrahedron Lett. 1990, 31, 2461-2462. For the phosphite-directed hydroformylation, see: Jackson, W. R.; Moffat, M. R.; Perlmutter, P.; Tasdelen, E. E. Aust. J. Chem. 1992, 45, 823-834.
13. 3. For examples of stereoselectivity in the rhodium-catalyzed hydroformylation, see: Lazzaroni, R.; Pucci, S.; Bertozzi, S.; Pini, D. J. Organomet Chem. 1983, 247, C56-58. Azzaroni, F.; Biscarini, P.; Bordoni, S.; Longoni, G.; Venturini, E. J. Organomet. Chem. 1996, 508, 59-67. For the phosphine-directed hydroformylation, see: Burke, S. D.; Cobb, J. E. Tetrahedron Lett. 1986, 27, 4237-4240. Burke, S. D.; Cobb, J. E.; Takeuchi, K. J. Org. Chem. 1990, 55, 2138-2151. Jackson, W. R.; Perlmutter, P.; Suh, G.-H. J. Chem. Soc., Chem. Commun. 1987, 724-725. Jackson, W. R.; Perlmutter, P.; Tasdelen, E. E. Tetrahedron Lett. 1990, 31, 2461-2462. For the phosphite-directed hydroformylation, see: Jackson, W. R.; Moffat, M. R.; Perlmutter, P.; Tasdelen, E. E. Aust. J. Chem. 1992, 45, 823-834.
14. 3. For examples of stereoselectivity in the rhodium-catalyzed hydroformylation, see: Lazzaroni, R.; Pucci, S.; Bertozzi, S.; Pini, D. J. Organomet Chem. 1983, 247, C56-58. Azzaroni, F.; Biscarini, P.; Bordoni, S.; Longoni, G.; Venturini, E. J. Organomet. Chem. 1996, 508, 59-67. For the phosphine-directed hydroformylation, see: Burke, S. D.; Cobb, J. E. Tetrahedron Lett. 1986, 27, 4237-4240. Burke, S. D.; Cobb, J. E.; Takeuchi, K. J. Org. Chem. 1990, 55, 2138-2151. Jackson, W. R.; Perlmutter, P.; Suh, G.-H. J. Chem. Soc., Chem. Commun. 1987, 724-725. Jackson, W. R.; Perlmutter, P.; Tasdelen, E. E. Tetrahedron Lett. 1990, 31, 2461-2462. For the phosphite-directed hydroformylation, see: Jackson, W. R.; Moffat, M. R.; Perlmutter, P.; Tasdelen, E. E. Aust. J. Chem. 1992, 45, 823-834.
15. 4. For simple examples of 1,1-disubstituted alkenes, see: Botteghi, C.; Consiglio, G.; Ceccarelii, G.; Stefani, A. J. Org. Chem. 1972, 37, 1835-1837. Hoffmann, W.; Siegel, H. Tetrahedron Lett. 1975, 533-526. Opposite regioselectivity, see: Kollár, L.; Consiglio, G.; Pino, P. Chimia 1986, 40, 428-429. Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623-632.
16. 4. For simple examples of 1,1-disubstituted alkenes, see: Botteghi, C.; Consiglio, G.; Ceccarelii, G.; Stefani, A. J. Org. Chem. 1972, 37, 1835-1837. Hoffmann, W.; Siegel, H. Tetrahedron Lett. 1975, 533-526. Opposite regioselectivity, see: Kollár, L.; Consiglio, G.; Pino, P. Chimia 1986, 40, 428-429. Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623-632.
17. 4. For simple examples of 1,1-disubstituted alkenes, see: Botteghi, C.; Consiglio, G.; Ceccarelii, G.; Stefani, A. J. Org. Chem. 1972, 37, 1835-1837. Hoffmann, W.; Siegel, H. Tetrahedron Lett. 1975, 533-526. Opposite regioselectivity, see: Kollár, L.; Consiglio, G.; Pino, P. Chimia 1986, 40, 428-429. Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623-632.
18. 4. For simple examples of 1,1-disubstituted alkenes, see: Botteghi, C.; Consiglio, G.; Ceccarelii, G.; Stefani, A. J. Org. Chem. 1972, 37, 1835-1837. Hoffmann, W.; Siegel, H. Tetrahedron Lett. 1975, 533-526. Opposite regioselectivity, see: Kollár, L.; Consiglio, G.; Pino, P. Chimia 1986, 40, 428-429. Gladiali, S.; Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623-632.
19. 5. For a review of homoenolates, see: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Heathcock, C. H. Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p.441.
20. 6. Brown, J. M. Angew. Chem., Int. Ed. Engl. 1987, 26, 190-203.
21. 7. Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1988, 110, 6917-6918. For a recent review of substrate-directed chemical reactions, see: Hoveyda, A. H; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
22. 7. Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1988, 110, 6917-6918. For a recent review of substrate-directed chemical reactions, see: Hoveyda, A. H; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
23. 8. No diastereoselection in the hydroformylation was observed where a chiral hydroxy substituent was present in the allylic position, see ref. 2a.
24. 9. The products 3a and 4a were observed as a diastereomer mixture of hemiacetals.
25. 4,which is effective in the hydroxy-directed hydrogenation (nbd = norbornadiene).
26. 11. Hydrogenation of 4-t-butylcyclohexanone catalyzed by a bulky iridium hydride or rhodium hydride species proceeds via equatorial attack (ca. 96%), see Org. Syn.; John Wiley & Sons Inc.: New York, 1988; Coll. Vol. 6, p 215
27. 12. The hydroformylation of 4-t-butylmethylenecyclohexane using the present catalyst precursor 1 gave rise to a 1 : 1 mixture of cis-and trans-4-t-butylcyclohexylacetaldehyde in quantitative yield.