Diastereoselective hydroformylation of acyclic olefins: Efficient construction of an all-anti stereotriade building block for polyketide synthesis

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 1901-1904

  Breit, Bernhard ^a   Zahn, Stephan K ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; POLYKETIDE;

ACETYLATION; ARTICLE; CATALYST; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; DRUG SYNTHESIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032473817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00158-0     Document Type: Article

References (36)

1. 1. a) B. M. Trost, Angew. Chem. 1995, 107, 285-307; Angew. Chem. Int. Ed. Engl. 1995, 34, 259;
2. 1. a) B. M. Trost, Angew. Chem. 1995, 107, 285-307; Angew. Chem. Int. Ed. Engl. 1995, 34, 259;
3. b) B. M. Trost, Science 1991, 254, 1471-1477.
4. 2. Selected reports on diastereoselective hydroformylation of cyclic olefins: A. L. Nussbaum, T. L. Popper, E. P. Oliveto, S. Friedman, I. Wender, J. Am. Chem. Soc. 1959, 81, 1228-1231; W. Himmele, H. Siegel Tetrahedron Lett. 1976, 907-910; D. Banach, G. O. Evans, D. G. McIntyre, T. Predmore, M. G. Richmond, J. H. Supple, R. P. Stewart, Jr., J. Mol. Catal. 1985, 31, 15; S. D. Burke, J. E. Cobb, Teterahedron Lett. 1986, 27, 4237-4240; W. R. Jackson, P. Perlmutter, E. E. Tasdelen, J. Chem. Soc., Chem. Commun. 1990, 763-764; L. Kollár, P. Sándor, J. Organomet. Chem. 1993, 445, 257-259; for recent outstanding results see J. L. Leighton, D. N. O'Neil, J. Am. Chem. Soc. 1997, 119, 11118-11119.
5. 2. Selected reports on diastereoselective hydroformylation of cyclic olefins: A. L. Nussbaum, T. L. Popper, E. P. Oliveto, S. Friedman, I. Wender, J. Am. Chem. Soc. 1959, 81, 1228-1231; W. Himmele, H. Siegel Tetrahedron Lett. 1976, 907-910; D. Banach, G. O. Evans, D. G. McIntyre, T. Predmore, M. G. Richmond, J. H. Supple, R. P. Stewart, Jr., J. Mol. Catal. 1985, 31, 15; S. D. Burke, J. E. Cobb, Teterahedron Lett. 1986, 27, 4237-4240; W. R. Jackson, P. Perlmutter, E. E. Tasdelen, J. Chem. Soc., Chem. Commun. 1990, 763-764; L. Kollár, P. Sándor, J. Organomet. Chem. 1993, 445, 257-259; for recent outstanding results see J. L. Leighton, D. N. O'Neil, J. Am. Chem. Soc. 1997, 119, 11118-11119.
6. 2. Selected reports on diastereoselective hydroformylation of cyclic olefins: A. L. Nussbaum, T. L. Popper, E. P. Oliveto, S. Friedman, I. Wender, J. Am. Chem. Soc. 1959, 81, 1228-1231; W. Himmele, H. Siegel Tetrahedron Lett. 1976, 907-910; D. Banach, G. O. Evans, D. G. McIntyre, T. Predmore, M. G. Richmond, J. H. Supple, R. P. Stewart, Jr., J. Mol. Catal. 1985, 31, 15; S. D. Burke, J. E. Cobb, Teterahedron Lett. 1986, 27, 4237-4240; W. R. Jackson, P. Perlmutter, E. E. Tasdelen, J. Chem. Soc., Chem. Commun. 1990, 763-764; L. Kollár, P. Sándor, J. Organomet. Chem. 1993, 445, 257-259; for recent outstanding results see J. L. Leighton, D. N. O'Neil, J. Am. Chem. Soc. 1997, 119, 11118-11119.
7. 2. Selected reports on diastereoselective hydroformylation of cyclic olefins: A. L. Nussbaum, T. L. Popper, E. P. Oliveto, S. Friedman, I. Wender, J. Am. Chem. Soc. 1959, 81, 1228-1231; W. Himmele, H. Siegel Tetrahedron Lett. 1976, 907-910; D. Banach, G. O. Evans, D. G. McIntyre, T. Predmore, M. G. Richmond, J. H. Supple, R. P. Stewart, Jr., J. Mol. Catal. 1985, 31, 15; S. D. Burke, J. E. Cobb, Teterahedron Lett. 1986, 27, 4237-4240; W. R. Jackson, P. Perlmutter, E. E. Tasdelen, J. Chem. Soc., Chem. Commun. 1990, 763-764; L. Kollár, P. Sándor, J. Organomet. Chem. 1993, 445, 257-259; for recent outstanding results see J. L. Leighton, D. N. O'Neil, J. Am. Chem. Soc. 1997, 119, 11118-11119.
8. 2. Selected reports on diastereoselective hydroformylation of cyclic olefins: A. L. Nussbaum, T. L. Popper, E. P. Oliveto, S. Friedman, I. Wender, J. Am. Chem. Soc. 1959, 81, 1228-1231; W. Himmele, H. Siegel Tetrahedron Lett. 1976, 907-910; D. Banach, G. O. Evans, D. G. McIntyre, T. Predmore, M. G. Richmond, J. H. Supple, R. P. Stewart, Jr., J. Mol. Catal. 1985, 31, 15; S. D. Burke, J. E. Cobb, Teterahedron Lett. 1986, 27, 4237-4240; W. R. Jackson, P. Perlmutter, E. E. Tasdelen, J. Chem. Soc., Chem. Commun. 1990, 763-764; L. Kollár, P. Sándor, J. Organomet. Chem. 1993, 445, 257-259; for recent outstanding results see J. L. Leighton, D. N. O'Neil, J. Am. Chem. Soc. 1997, 119, 11118-11119.
9. 2. Selected reports on diastereoselective hydroformylation of cyclic olefins: A. L. Nussbaum, T. L. Popper, E. P. Oliveto, S. Friedman, I. Wender, J. Am. Chem. Soc. 1959, 81, 1228-1231; W. Himmele, H. Siegel Tetrahedron Lett. 1976, 907-910; D. Banach, G. O. Evans, D. G. McIntyre, T. Predmore, M. G. Richmond, J. H. Supple, R. P. Stewart, Jr., J. Mol. Catal. 1985, 31, 15; S. D. Burke, J. E. Cobb, Teterahedron Lett. 1986, 27, 4237-4240; W. R. Jackson, P. Perlmutter, E. E. Tasdelen, J. Chem. Soc., Chem. Commun. 1990, 763-764; L. Kollár, P. Sándor, J. Organomet. Chem. 1993, 445, 257-259; for recent outstanding results see J. L. Leighton, D. N. O'Neil, J. Am. Chem. Soc. 1997, 119, 11118-11119.
10. 2. Selected reports on diastereoselective hydroformylation of cyclic olefins: A. L. Nussbaum, T. L. Popper, E. P. Oliveto, S. Friedman, I. Wender, J. Am. Chem. Soc. 1959, 81, 1228-1231; W. Himmele, H. Siegel Tetrahedron Lett. 1976, 907-910; D. Banach, G. O. Evans, D. G. McIntyre, T. Predmore, M. G. Richmond, J. H. Supple, R. P. Stewart, Jr., J. Mol. Catal. 1985, 31, 15; S. D. Burke, J. E. Cobb, Teterahedron Lett. 1986, 27, 4237-4240; W. R. Jackson, P. Perlmutter, E. E. Tasdelen, J. Chem. Soc., Chem. Commun. 1990, 763-764; L. Kollár, P. Sándor, J. Organomet. Chem. 1993, 445, 257-259; for recent outstanding results see J. L. Leighton, D. N. O'Neil, J. Am. Chem. Soc. 1997, 119, 11118-11119.
11. 3. Selected reports on diastereoselective hydroformylation of acyclic olefins: P. Pino, J. Organomet. Chem. 1980, 200, 223-242; R. Lazzaroni, S. Pucci, S. Bertozzi, D. Pin, J. Organomet. Chem. 1983, 247, C56-C58; J. Brocard, L. Pélinski, L. Maciejewski, S. Naili, H. Bricout, A. Mortreux, F. Petit, J. Organomet. Chem. 1994, 483, C1-C5; T. Doi, H. Komatsu, K. Yamamoto, Tetrahedron Lett. 1996, 37, 6877-6880; see also ref. 6 and 9.
12. 3. Selected reports on diastereoselective hydroformylation of acyclic olefins: P. Pino, J. Organomet. Chem. 1980, 200, 223-242; R. Lazzaroni, S. Pucci, S. Bertozzi, D. Pin, J. Organomet. Chem. 1983, 247, C56-C58; J. Brocard, L. Pélinski, L. Maciejewski, S. Naili, H. Bricout, A. Mortreux, F. Petit, J. Organomet. Chem. 1994, 483, C1-C5; T. Doi, H. Komatsu, K. Yamamoto, Tetrahedron Lett. 1996, 37, 6877-6880; see also ref. 6 and 9.
13. 3. Selected reports on diastereoselective hydroformylation of acyclic olefins: P. Pino, J. Organomet. Chem. 1980, 200, 223-242; R. Lazzaroni, S. Pucci, S. Bertozzi, D. Pin, J. Organomet. Chem. 1983, 247, C56-C58; J. Brocard, L. Pélinski, L. Maciejewski, S. Naili, H. Bricout, A. Mortreux, F. Petit, J. Organomet. Chem. 1994, 483, C1-C5; T. Doi, H. Komatsu, K. Yamamoto, Tetrahedron Lett. 1996, 37, 6877-6880; see also ref. 6 and 9.
14. 3. Selected reports on diastereoselective hydroformylation of acyclic olefins: P. Pino, J. Organomet. Chem. 1980, 200, 223-242; R. Lazzaroni, S. Pucci, S. Bertozzi, D. Pin, J. Organomet. Chem. 1983, 247, C56-C58; J. Brocard, L. Pélinski, L. Maciejewski, S. Naili, H. Bricout, A. Mortreux, F. Petit, J. Organomet. Chem. 1994, 483, C1-C5; T. Doi, H. Komatsu, K. Yamamoto, Tetrahedron Lett. 1996, 37, 6877-6880; see also ref. 6 and 9.
15. 4. For a definition of the term Stereotriade see: R. W. Hoffmann, Angew. Chem. 1987, 99, 503-610; Angew. Chem. Int. Ed. Engl. 1987, 26, 489-503.
16. 4. For a definition of the term Stereotriade see: R. W. Hoffmann, Angew. Chem. 1987, 99, 503-610; Angew. Chem. Int. Ed. Engl. 1987, 26, 489-503.
17. 5. F. H. Jardine, Polyhedron 1982, 1, 569-605; T. Ziegler, L. Versluis, Advances in Chemistry Series 1992, 230, 75-93; P. W. N. M. van Leeuwen, G. van Koten, Studies Surf. Sci. Catal. 1993, 79, 199; T. Horiuchi, E. Shirakawa, K. Nozaki, H. Takaya, Organometallics 1997, 16, 2981-2986; C. P. Casey, L. M. Petrovich, J. Am. Chem. Soc. 1995, 117, 6007-6014.
18. 5. F. H. Jardine, Polyhedron 1982, 1, 569-605; T. Ziegler, L. Versluis, Advances in Chemistry Series 1992, 230, 75-93; P. W. N. M. van Leeuwen, G. van Koten, Studies Surf. Sci. Catal. 1993, 79, 199; T. Horiuchi, E. Shirakawa, K. Nozaki, H. Takaya, Organometallics 1997, 16, 2981-2986; C. P. Casey, L. M. Petrovich, J. Am. Chem. Soc. 1995, 117, 6007-6014.
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