Preparation of titanated alkoxyallenes from 3-alkoxy-2-propyn-1-yl carbonates and (η2-propene)Ti(O-i-Pr)2 as an efficient ester homoaldol equivalent

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2369-2371

  Hanazawa, Takeshi ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

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Indexed keywords

EID: 0000014847     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006142f     Document Type: Article

References (25)

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2. Titanium ester homoenolates: Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1983, 105, 651. Goswami, R. J. Org. Chem. 1985, 50, 5907.
3. Titanium ester homoenolates: Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1983, 105, 651. Goswami, R. J. Org. Chem. 1985, 50, 5907.
4. Titanium ester homoenolates: Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745. Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1983, 105, 651. Goswami, R. J. Org. Chem. 1985, 50, 5907.
5. Reviews for homoenolates and their equivalents, see: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
6. Reviews for homoenolates and their equivalents, see: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
7. Reviews for homoenolates and their equivalents, see: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
8. Reviews for homoenolates and their equivalents, see: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
9. Reviews for homoenolates and their equivalents, see: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
10. Reviews for homoenolates and their equivalents, see: Kuwajima, I.; Nakamura, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 441. Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1. Ryu, I.; Sonoda, N. Synth. Org. Chem., Jpn. 1985, 43, 112. Werstiuk, N. H. Tetrahedron 1983, 39, 205. Katritzky, A. R.; Piffl, M.; Lang, H.; Anders, E. Chem. Rev. 1999, 99, 665. See also; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
11. Nakagawa, T.; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 3207. Yoshida, Y.; Nakagawa, T.; Sato, F. Synlett 1996, 437. Kasatkin, A.; Sato; F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2848. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4861. An, D. K.; Hirakawa, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 3737. Okamoto, S.; An, D. K.; Sato, F. Tetrahedron Lett. 1998, 39, 4551. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4555.
12. Nakagawa, T.; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 3207. Yoshida, Y.; Nakagawa, T.; Sato, F. Synlett 1996, 437. Kasatkin, A.; Sato; F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2848. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4861. An, D. K.; Hirakawa, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 3737. Okamoto, S.; An, D. K.; Sato, F. Tetrahedron Lett. 1998, 39, 4551. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4555.
13. Nakagawa, T.; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 3207. Yoshida, Y.; Nakagawa, T.; Sato, F. Synlett 1996, 437. Kasatkin, A.; Sato; F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2848. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4861. An, D. K.; Hirakawa, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 3737. Okamoto, S.; An, D. K.; Sato, F. Tetrahedron Lett. 1998, 39, 4551. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4555.
14. Nakagawa, T.; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 3207. Yoshida, Y.; Nakagawa, T.; Sato, F. Synlett 1996, 437. Kasatkin, A.; Sato; F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2848. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4861. An, D. K.; Hirakawa, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 3737. Okamoto, S.; An, D. K.; Sato, F. Tetrahedron Lett. 1998, 39, 4551. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4555.
15. Nakagawa, T.; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 3207. Yoshida, Y.; Nakagawa, T.; Sato, F. Synlett 1996, 437. Kasatkin, A.; Sato; F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2848. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4861. An, D. K.; Hirakawa, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 3737. Okamoto, S.; An, D. K.; Sato, F. Tetrahedron Lett. 1998, 39, 4551. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4555.
16. Nakagawa, T.; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 3207. Yoshida, Y.; Nakagawa, T.; Sato, F. Synlett 1996, 437. Kasatkin, A.; Sato; F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2848. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4861. An, D. K.; Hirakawa, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 3737. Okamoto, S.; An, D. K.; Sato, F. Tetrahedron Lett. 1998, 39, 4551. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4555.
17. Nakagawa, T.; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 3207. Yoshida, Y.; Nakagawa, T.; Sato, F. Synlett 1996, 437. Kasatkin, A.; Sato; F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2848. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4861. An, D. K.; Hirakawa, K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1999, 40, 3737. Okamoto, S.; An, D. K.; Sato, F. Tetrahedron Lett. 1998, 39, 4551. An, D. K.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1998, 39, 4555.
18. 2. see: Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511. Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753. Sato, F.; Urabe, H.; Okamoto, S. J. Synth. Org. Chem. Jpn. 1998, 56, 424.
19. 2. see: Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511. Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753. Sato, F.; Urabe, H.; Okamoto, S. J. Synth. Org. Chem. Jpn. 1998, 56, 424.
20. 2. see: Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511. Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753. Sato, F.; Urabe, H.; Okamoto, S. J. Synth. Org. Chem. Jpn. 1998, 56, 424.
21. Porter, N. A.; Dussault, P.; Breyer, R. A.; Kaplan, J.; Morelli, J. Chem. Res. Toxicol. 1990, 3, 236. Moyano, A.; Charbonnier, F.; Greene, A. E. J. Org. Chem. 1987, 52, 2919.
22. Porter, N. A.; Dussault, P.; Breyer, R. A.; Kaplan, J.; Morelli, J. Chem. Res. Toxicol. 1990, 3, 236. Moyano, A.; Charbonnier, F.; Greene, A. E. J. Org. Chem. 1987, 52, 2919.
23. The starting carbonate for the reaction of Scheme 5 and Scheme 6 could readily be prepared from the corresponding alcohol and aldehyde according to a similar procedure shown in Scheme 3 in 70% and 72% overall yield, respectively.
24. 13C NMR analyses. The stereochemistries of the products were not determined.
25. For a review of chiral homoenolate equivalents, see: Ahlbrecht, H.; Beyer, U. Synthesis 1999, 365.