1,3-asymmetric induction in stereoselective rhodium-catalyzed hydroformylation of homomethallylic alcohols

European Journal of Organic Chemistry

Volumn , Issue 6, 1998, Pages 1123-1134

  Breit, Bernhard ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Asymmetric synthesis; Catalysis; Catalyst directing groups; Hydroformylations; Rhodium compounds

Indexed keywords

EID: 2742537764     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199806)1998:6<1123::AID-EJOC1123>3.0.CO;2-Y     Document Type: Article

References (59)

1. See for example: [1a] M. Sakai, S. Mano, K. Nozaki, H. Takaya, J. Am. Chem. Soc 1993, 115, 7033-7034. [1b] F. Agbossou, J.-F. Carpentier, A. Mortreux, Chem. Rev. 1995, 95, 2485-2506. [1c] B. M Trost, Ace. Chem. Res. 1996, 29, 355-364. [1d] M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1311; Angew: Chem. Int. Ed. Engl. 1997, 36, 1236-1256.
2. See for example: [1a] M. Sakai, S. Mano, K. Nozaki, H. Takaya, J. Am. Chem. Soc 1993, 115, 7033-7034. [1b] F. Agbossou, J.-F. Carpentier, A. Mortreux, Chem. Rev. 1995, 95, 2485-2506. [1c] B. M Trost, Ace. Chem. Res. 1996, 29, 355-364. [1d] M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1311; Angew: Chem. Int. Ed. Engl. 1997, 36, 1236-1256.
3. See for example: [1a] M. Sakai, S. Mano, K. Nozaki, H. Takaya, J. Am. Chem. Soc 1993, 115, 7033-7034. [1b] F. Agbossou, J.-F. Carpentier, A. Mortreux, Chem. Rev. 1995, 95, 2485-2506. [1c] B. M Trost, Ace. Chem. Res. 1996, 29, 355-364. [1d] M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1311; Angew: Chem. Int. Ed. Engl. 1997, 36, 1236-1256.
4. See for example: [1a] M. Sakai, S. Mano, K. Nozaki, H. Takaya, J. Am. Chem. Soc 1993, 115, 7033-7034. [1b] F. Agbossou, J.-F. Carpentier, A. Mortreux, Chem. Rev. 1995, 95, 2485-2506. [1c] B. M Trost, Ace. Chem. Res. 1996, 29, 355-364. [1d] M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1311; Angew: Chem. Int. Ed. Engl. 1997, 36, 1236-1256.
5. See for example: [1a] M. Sakai, S. Mano, K. Nozaki, H. Takaya, J. Am. Chem. Soc 1993, 115, 7033-7034. [1b] F. Agbossou, J.-F. Carpentier, A. Mortreux, Chem. Rev. 1995, 95, 2485-2506. [1c] B. M Trost, Ace. Chem. Res. 1996, 29, 355-364. [1d] M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1311; Angew: Chem. Int. Ed. Engl. 1997, 36, 1236-1256.
6. A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev 1993, 93, 1307-1370.
7. [4][5][7]. For substrate directed transition metal catalysed reduction processes see: J. M. Brown, Angew. Chem. 1987, 99, 169-182; Angew. Chem. Int. Ed. Engl. 1987, 26, 190-203; D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc 1992, 114, 6671-6679; K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179-1191.
8. [4][5][7]. For substrate directed transition metal catalysed reduction processes see: J. M. Brown, Angew. Chem. 1987, 99, 169-182; Angew. Chem. Int. Ed. Engl. 1987, 26, 190-203; D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc 1992, 114, 6671-6679; K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179-1191.
9. [4][5][7]. For substrate directed transition metal catalysed reduction processes see: J. M. Brown, Angew. Chem. 1987, 99, 169-182; Angew. Chem. Int. Ed. Engl. 1987, 26, 190-203; D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc 1992, 114, 6671-6679; K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179-1191.
10. [4][5][7]. For substrate directed transition metal catalysed reduction processes see: J. M. Brown, Angew. Chem. 1987, 99, 169-182; Angew. Chem. Int. Ed. Engl. 1987, 26, 190-203; D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc 1992, 114, 6671-6679; K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179-1191.
11. [4][5][7]. For substrate directed transition metal catalysed reduction processes see: J. M. Brown, Angew. Chem. 1987, 99, 169-182; Angew. Chem. Int. Ed. Engl. 1987, 26, 190-203; D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc 1992, 114, 6671-6679; K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179-1191.
12. [4][5][7]. For substrate directed transition metal catalysed reduction processes see: J. M. Brown, Angew. Chem. 1987, 99, 169-182; Angew. Chem. Int. Ed. Engl. 1987, 26, 190-203; D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc 1992, 114, 6671-6679; K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179-1191.
13. [4][5][7]. For substrate directed transition metal catalysed reduction processes see: J. M. Brown, Angew. Chem. 1987, 99, 169-182; Angew. Chem. Int. Ed. Engl. 1987, 26, 190-203; D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc 1992, 114, 6671-6679; K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179-1191.
14. [4a] B. Breit, Angew. Chem. 1996, 108. 3021-3023; Angew. Chem. Int. Ed. Engl. 1996, 35, 2835-2837.
15. [4a] B. Breit, Angew. Chem. 1996, 108. 3021-3023; Angew. Chem. Int. Ed. Engl. 1996, 35, 2835-2837.
16. [4b] B. Breit, Liebigs Ann. 1997, 1841-1851.
17. [4c] B. Breit in Organic Synthesis via Organometallics (Eds.: G. Helmchen, J. Dibo, D. Flubacher, B. Wiese), Vieweg, Braunschweig, 1997, 139-146.
18. For a review on stereoselective hydroformylations, see: [5a] P. Eilbracht in Houben-Weyl, Methods of Organic Synthesis, E 21, Stereoselective Synthesis. (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, p. 2488-2557. For substrate-directed diastereoselective hydroformylation of cyclic systems, see: [5b] S. D. Burke, J. E. Cobb, Tetrahedron Lett. 1986, 27, 4237-4240. [5c] W. R. Jackson, P. Perlmutter, E. E. Tasdelen, J. Chem. Soc., Chem. Commun. 1990, 763-764.
19. For a review on stereoselective hydroformylations, see: [5a] P. Eilbracht in Houben-Weyl, Methods of Organic Synthesis, E 21, Stereoselective Synthesis. (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, p. 2488-2557. For substrate-directed diastereoselective hydroformylation of cyclic systems, see: [5b] S. D. Burke, J. E. Cobb, Tetrahedron Lett. 1986, 27, 4237-4240. [5c] W. R. Jackson, P. Perlmutter, E. E. Tasdelen, J. Chem. Soc., Chem. Commun. 1990, 763-764.
20. For a review on stereoselective hydroformylations, see: [5a] P. Eilbracht in Houben-Weyl, Methods of Organic Synthesis, E 21, Stereoselective Synthesis. (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, p. 2488-2557. For substrate-directed diastereoselective hydroformylation of cyclic systems, see: [5b] S. D. Burke, J. E. Cobb, Tetrahedron Lett. 1986, 27, 4237-4240. [5c] W. R. Jackson, P. Perlmutter, E. E. Tasdelen, J. Chem. Soc., Chem. Commun. 1990, 763-764.
21. See for example: [6a] FK506: H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto, T. Taga, J. Am Chem. Soc. 1987, 109, 5031-5033; T Kino, H. Hatanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 1249. [6b] Aplyronine A/B/C: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, M. Arakawa, J. Am. Chem. Soc. 1993, 115, 11020-11021. [6c] Palytoxin: J. K. Cha, W. J. Christ, J. M. Finan, H. Fujioka, Y. Kishi, L. L. Klein, S. S. Ko, J. Leder, W. W. McWhorter, Jr., K.-P. Pfaff, M. Yonaga, D. Uemura, Y. Hirata, J. Am. Chem. Soc. 1982, 104, 7369-7371. [6d] Herbimycin: S. Omura, A. Nakagawa, N. Sadakane, Tetrahedron Lett. 1979, 4323-4326. [6e] side chain of Maitotoxin: M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1782-1785; Angew. Chem. Int. Ed. Engl. 1996, 35, 1672. [6f] AAL-toxin TA1: A. T. Bottini, D. G. Gilchrist. Tetrahedron Lett. 1981, 22, 2719-2722. [6g] Fumonisin B1: S. C. Bezuidenhout, W. C. A. Gelderblom, C. P. Gorst-Allman, R. M. Horak, W. F. O. Marasas, G. Spiteller, R. Vleggaar, J. Chem. Soc., Chem. Commun. 1988, 743-745.
22. See for example: [6a] FK506: H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto, T. Taga, J. Am Chem. Soc. 1987, 109, 5031-5033; T Kino, H. Hatanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 1249. [6b] Aplyronine A/B/C: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, M. Arakawa, J. Am. Chem. Soc. 1993, 115, 11020-11021. [6c] Palytoxin: J. K. Cha, W. J. Christ, J. M. Finan, H. Fujioka, Y. Kishi, L. L. Klein, S. S. Ko, J. Leder, W. W. McWhorter, Jr., K.-P. Pfaff, M. Yonaga, D. Uemura, Y. Hirata, J. Am. Chem. Soc. 1982, 104, 7369-7371. [6d] Herbimycin: S. Omura, A. Nakagawa, N. Sadakane, Tetrahedron Lett. 1979, 4323-4326. [6e] side chain of Maitotoxin: M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1782-1785; Angew. Chem. Int. Ed. Engl. 1996, 35, 1672. [6f] AAL-toxin TA1: A. T. Bottini, D. G. Gilchrist. Tetrahedron Lett. 1981, 22, 2719-2722. [6g] Fumonisin B1: S. C. Bezuidenhout, W. C. A. Gelderblom, C. P. Gorst-Allman, R. M. Horak, W. F. O. Marasas, G. Spiteller, R. Vleggaar, J. Chem. Soc., Chem. Commun. 1988, 743-745.
23. See for example: [6a] FK506: H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto, T. Taga, J. Am Chem. Soc. 1987, 109, 5031-5033; T Kino, H. Hatanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 1249. [6b] Aplyronine A/B/C: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, M. Arakawa, J. Am. Chem. Soc. 1993, 115, 11020-11021. [6c] Palytoxin: J. K. Cha, W. J. Christ, J. M. Finan, H. Fujioka, Y. Kishi, L. L. Klein, S. S. Ko, J. Leder, W. W. McWhorter, Jr., K.-P. Pfaff, M. Yonaga, D. Uemura, Y. Hirata, J. Am. Chem. Soc. 1982, 104, 7369-7371. [6d] Herbimycin: S. Omura, A. Nakagawa, N. Sadakane, Tetrahedron Lett. 1979, 4323-4326. [6e] side chain of Maitotoxin: M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1782-1785; Angew. Chem. Int. Ed. Engl. 1996, 35, 1672. [6f] AAL-toxin TA1: A. T. Bottini, D. G. Gilchrist. Tetrahedron Lett. 1981, 22, 2719-2722. [6g] Fumonisin B1: S. C. Bezuidenhout, W. C. A. Gelderblom, C. P. Gorst-Allman, R. M. Horak, W. F. O. Marasas, G. Spiteller, R. Vleggaar, J. Chem. Soc., Chem. Commun. 1988, 743-745.
24. See for example: [6a] FK506: H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto, T. Taga, J. Am Chem. Soc. 1987, 109, 5031-5033; T Kino, H. Hatanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 1249. [6b] Aplyronine A/B/C: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, M. Arakawa, J. Am. Chem. Soc. 1993, 115, 11020-11021. [6c] Palytoxin: J. K. Cha, W. J. Christ, J. M. Finan, H. Fujioka, Y. Kishi, L. L. Klein, S. S. Ko, J. Leder, W. W. McWhorter, Jr., K.-P. Pfaff, M. Yonaga, D. Uemura, Y. Hirata, J. Am. Chem. Soc. 1982, 104, 7369-7371. [6d] Herbimycin: S. Omura, A. Nakagawa, N. Sadakane, Tetrahedron Lett. 1979, 4323-4326. [6e] side chain of Maitotoxin: M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1782-1785; Angew. Chem. Int. Ed. Engl. 1996, 35, 1672. [6f] AAL-toxin TA1: A. T. Bottini, D. G. Gilchrist. Tetrahedron Lett. 1981, 22, 2719-2722. [6g] Fumonisin B1: S. C. Bezuidenhout, W. C. A. Gelderblom, C. P. Gorst-Allman, R. M. Horak, W. F. O. Marasas, G. Spiteller, R. Vleggaar, J. Chem. Soc., Chem. Commun. 1988, 743-745.
25. See for example: [6a] FK506: H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto, T. Taga, J. Am Chem. Soc. 1987, 109, 5031-5033; T Kino, H. Hatanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 1249. [6b] Aplyronine A/B/C: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, M. Arakawa, J. Am. Chem. Soc. 1993, 115, 11020-11021. [6c] Palytoxin: J. K. Cha, W. J. Christ, J. M. Finan, H. Fujioka, Y. Kishi, L. L. Klein, S. S. Ko, J. Leder, W. W. McWhorter, Jr., K.-P. Pfaff, M. Yonaga, D. Uemura, Y. Hirata, J. Am. Chem. Soc. 1982, 104, 7369-7371. [6d] Herbimycin: S. Omura, A. Nakagawa, N. Sadakane, Tetrahedron Lett. 1979, 4323-4326. [6e] side chain of Maitotoxin: M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1782-1785; Angew. Chem. Int. Ed. Engl. 1996, 35, 1672. [6f] AAL-toxin TA1: A. T. Bottini, D. G. Gilchrist. Tetrahedron Lett. 1981, 22, 2719-2722. [6g] Fumonisin B1: S. C. Bezuidenhout, W. C. A. Gelderblom, C. P. Gorst-Allman, R. M. Horak, W. F. O. Marasas, G. Spiteller, R. Vleggaar, J. Chem. Soc., Chem. Commun. 1988, 743-745.
26. See for example: [6a] FK506: H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto, T. Taga, J. Am Chem. Soc. 1987, 109, 5031-5033; T Kino, H. Hatanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 1249. [6b] Aplyronine A/B/C: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, M. Arakawa, J. Am. Chem. Soc. 1993, 115, 11020-11021. [6c] Palytoxin: J. K. Cha, W. J. Christ, J. M. Finan, H. Fujioka, Y. Kishi, L. L. Klein, S. S. Ko, J. Leder, W. W. McWhorter, Jr., K.-P. Pfaff, M. Yonaga, D. Uemura, Y. Hirata, J. Am. Chem. Soc. 1982, 104, 7369-7371. [6d] Herbimycin: S. Omura, A. Nakagawa, N. Sadakane, Tetrahedron Lett. 1979, 4323-4326. [6e] side chain of Maitotoxin: M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1782-1785; Angew. Chem. Int. Ed. Engl. 1996, 35, 1672. [6f] AAL-toxin TA1: A. T. Bottini, D. G. Gilchrist. Tetrahedron Lett. 1981, 22, 2719-2722. [6g] Fumonisin B1: S. C. Bezuidenhout, W. C. A. Gelderblom, C. P. Gorst-Allman, R. M. Horak, W. F. O. Marasas, G. Spiteller, R. Vleggaar, J. Chem. Soc., Chem. Commun. 1988, 743-745.
27. See for example: [6a] FK506: H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto, T. Taga, J. Am Chem. Soc. 1987, 109, 5031-5033; T Kino, H. Hatanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 1249. [6b] Aplyronine A/B/C: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, M. Arakawa, J. Am. Chem. Soc. 1993, 115, 11020-11021. [6c] Palytoxin: J. K. Cha, W. J. Christ, J. M. Finan, H. Fujioka, Y. Kishi, L. L. Klein, S. S. Ko, J. Leder, W. W. McWhorter, Jr., K.-P. Pfaff, M. Yonaga, D. Uemura, Y. Hirata, J. Am. Chem. Soc. 1982, 104, 7369-7371. [6d] Herbimycin: S. Omura, A. Nakagawa, N. Sadakane, Tetrahedron Lett. 1979, 4323-4326. [6e] side chain of Maitotoxin: M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1782-1785; Angew. Chem. Int. Ed. Engl. 1996, 35, 1672. [6f] AAL-toxin TA1: A. T. Bottini, D. G. Gilchrist. Tetrahedron Lett. 1981, 22, 2719-2722. [6g] Fumonisin B1: S. C. Bezuidenhout, W. C. A. Gelderblom, C. P. Gorst-Allman, R. M. Horak, W. F. O. Marasas, G. Spiteller, R. Vleggaar, J. Chem. Soc., Chem. Commun. 1988, 743-745.
28. See for example: [6a] FK506: H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto, T. Taga, J. Am Chem. Soc. 1987, 109, 5031-5033; T Kino, H. Hatanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 1249. [6b] Aplyronine A/B/C: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, M. Arakawa, J. Am. Chem. Soc. 1993, 115, 11020-11021. [6c] Palytoxin: J. K. Cha, W. J. Christ, J. M. Finan, H. Fujioka, Y. Kishi, L. L. Klein, S. S. Ko, J. Leder, W. W. McWhorter, Jr., K.-P. Pfaff, M. Yonaga, D. Uemura, Y. Hirata, J. Am. Chem. Soc. 1982, 104, 7369-7371. [6d] Herbimycin: S. Omura, A. Nakagawa, N. Sadakane, Tetrahedron Lett. 1979, 4323-4326. [6e] side chain of Maitotoxin: M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1782-1785; Angew. Chem. Int. Ed. Engl. 1996, 35, 1672. [6f] AAL-toxin TA1: A. T. Bottini, D. G. Gilchrist. Tetrahedron Lett. 1981, 22, 2719-2722. [6g] Fumonisin B1: S. C. Bezuidenhout, W. C. A. Gelderblom, C. P. Gorst-Allman, R. M. Horak, W. F. O. Marasas, G. Spiteller, R. Vleggaar, J. Chem. Soc., Chem. Commun. 1988, 743-745.
29. See for example: [6a] FK506: H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto, T. Taga, J. Am Chem. Soc. 1987, 109, 5031-5033; T Kino, H. Hatanaka, M. Hashimoto, M. Nishiyama, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 1249. [6b] Aplyronine A/B/C: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, M. Arakawa, J. Am. Chem. Soc. 1993, 115, 11020-11021. [6c] Palytoxin: J. K. Cha, W. J. Christ, J. M. Finan, H. Fujioka, Y. Kishi, L. L. Klein, S. S. Ko, J. Leder, W. W. McWhorter, Jr., K.-P. Pfaff, M. Yonaga, D. Uemura, Y. Hirata, J. Am. Chem. Soc. 1982, 104, 7369-7371. [6d] Herbimycin: S. Omura, A. Nakagawa, N. Sadakane, Tetrahedron Lett. 1979, 4323-4326. [6e] side chain of Maitotoxin: M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. 1996, 108, 1782-1785; Angew. Chem. Int. Ed. Engl. 1996, 35, 1672. [6f] AAL-toxin TA1: A. T. Bottini, D. G. Gilchrist. Tetrahedron Lett. 1981, 22, 2719-2722. [6g] Fumonisin B1: S. C. Bezuidenhout, W. C. A. Gelderblom, C. P. Gorst-Allman, R. M. Horak, W. F. O. Marasas, G. Spiteller, R. Vleggaar, J. Chem. Soc., Chem. Commun. 1988, 743-745.
30. Parts of this work have been published previously as a preliminary communication: B. Breit, J. Chem. Soc., Chem. Commun. 1997, 591-592.
31. T. Imai, S. Nishida, Synthesis 1993, 395-399.
32. 3 under similar hydroformylation conditions (conversion of 5a after 24 h at 9O°C: quantitative) gave a complicated mixture of different products,which contained only minor amounts of the lactols 6.
33. B. Bardili, H. Marschall-Weyerstahl, P. Weyerstahl, Liebigs Ann. Chem. 1985, 275-300.
34. G. Höfle, W. Steglich, H. Vorbrüggen. Angew. Chem. 1978, 90, 602-615; Angew. Chem. Int. Ed. Engl 1978, 17, 569-583.
35. G. Höfle, W. Steglich, H. Vorbrüggen. Angew. Chem. 1978, 90, 602-615; Angew. Chem. Int. Ed. Engl 1978, 17, 569-583.
36. [4].
37. For determination of the relative configuration of the aldehydes 14, they were transformed in a similar manner as the o-DPPB derivative 10a via the corresponding dimethyl acetal lib into the alcohol 12 (syn:anti, 71:29). For details, see the Experimental Section.
38. For the combined use of vicinal coupling constants, 2D NOESY and MM3 force field calculations to determine preferred conformations of acyclic molecules in solution, see: R. Göttlich, C. Kahrs, J. Krüger, R. W. Hoffmann, J. Chem. Soc., Chem. Commun. 1997, 247-251; R. Göttlich, U. Schopfer, M. Stahl, R. W. Hoffmann, Liebigs Ann. 1997, 1757-1764; R. J. Smith, D. H. Williams, I C. J. Barna, I. R. McDermott, K. D. Haegele, F. Piriou. J. Wagner, W. Higgins, J. Am. Chem. Soc 1985. 107, 2849-2857; D. Neuhaus, M. P. Williamson, "The Nuclear Overhauser Effect in Structural and Conformational Analysis", VCH, New York 1989, pp 412; ibid, Chapter 11.
39. For the combined use of vicinal coupling constants, 2D NOESY and MM3 force field calculations to determine preferred conformations of acyclic molecules in solution, see: R. Göttlich, C. Kahrs, J. Krüger, R. W. Hoffmann, J. Chem. Soc., Chem. Commun. 1997, 247-251; R. Göttlich, U. Schopfer, M. Stahl, R. W. Hoffmann, Liebigs Ann. 1997, 1757-1764; R. J. Smith, D. H. Williams, I C. J. Barna, I. R. McDermott, K. D. Haegele, F. Piriou. J. Wagner, W. Higgins, J. Am. Chem. Soc 1985. 107, 2849-2857; D. Neuhaus, M. P. Williamson, "The Nuclear Overhauser Effect in Structural and Conformational Analysis", VCH, New York 1989, pp 412; ibid, Chapter 11.
40. For the combined use of vicinal coupling constants, 2D NOESY and MM3 force field calculations to determine preferred conformations of acyclic molecules in solution, see: R. Göttlich, C. Kahrs, J. Krüger, R. W. Hoffmann, J. Chem. Soc., Chem. Commun. 1997, 247-251; R. Göttlich, U. Schopfer, M. Stahl, R. W. Hoffmann, Liebigs Ann. 1997, 1757-1764; R. J. Smith, D. H. Williams, I C. J. Barna, I. R. McDermott, K. D. Haegele, F. Piriou. J. Wagner, W. Higgins, J. Am. Chem. Soc 1985. 107, 2849-2857; D. Neuhaus, M. P. Williamson, "The Nuclear Overhauser Effect in Structural and Conformational Analysis", VCH, New York 1989, pp 412; ibid, Chapter 11.
41. For the combined use of vicinal coupling constants, 2D NOESY and MM3 force field calculations to determine preferred conformations of acyclic molecules in solution, see: R. Göttlich, C. Kahrs, J. Krüger, R. W. Hoffmann, J. Chem. Soc., Chem. Commun. 1997, 247-251; R. Göttlich, U. Schopfer, M. Stahl, R. W. Hoffmann, Liebigs Ann. 1997, 1757-1764; R. J. Smith, D. H. Williams, I C. J. Barna, I. R. McDermott, K. D. Haegele, F. Piriou. J. Wagner, W. Higgins, J. Am. Chem. Soc 1985. 107, 2849-2857; D. Neuhaus, M. P. Williamson, "The Nuclear Overhauser Effect in Structural and Conformational Analysis", VCH, New York 1989, pp 412; ibid, Chapter 11.
42. 8]toluene, digital resolution: 0.125 Hz/pt). These data indicate a change in conformer populations for 10a on going to higher temperatures, which is reflected in the temperature dependence of the diastereoselectivities of the hydroformylation reaction.
43. 2 unit and the isopropyl substituent with identical conformation of the main chain have been combined additively.
44. [4]).
45. R. W. Hoffmann, Angew. Chem. 1992, 104, 1147-1157; Angew. Chem. Int. Ed. Engl. 1992, 31, 1124.
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