Synthesis of medium- and large-sized lactones in an aqueous-organic biphasic system

Angewandte Chemie - International Edition

Volumn 44, Issue 16, 2005, Pages 2397-2400

  Kinoshita, Hidenori ^a   Shinokubo, Hiroshi ^a,b   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Allylation; Biphasic catalysis; Lactones; Palladium; Solvent effects

Indexed keywords

BIPHASIC SYSTEM; LACTONES; MACROCYCLIZATION; TSUJI-TROST REACTION;

ADDITION REACTIONS; MOLECULAR DYNAMICS; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

KETONES;

LACTONE; ORGANIC COMPOUND; WATER;

ARTICLE; CHEMISTRY; SYNTHESIS;

LACTONES; ORGANIC CHEMICALS; WATER;

EID: 18044388948     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462677     Document Type: Article

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18. The aqueous Tsuji-Trost reaction has been extensively investigated. For selected examples, see: a) M. Safi, D. Sinou, Tetrahedron Lett. 1991, 32, 2025; b) J. P. Genêt, E. Blart, M. Savignac, Synlett 1992, 715; c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, D. Sinou, Tetrahedron 1994, 50, 505; d) S. Kobayashi, W.W.-L. Lam, K. Manabe, Tetrahedron Lett. 2000, 41. 6115; e) H. Danjo, D. Tanaka, T. Hayashi, Y. Uozumi, Tetrahedron 1999, 55, 14341; f) Y. Uozumi, K. Shibatomi, J. Am. Chem. Soc. 2001, 123, 2919; g) D. E. Bergbreiter, Y.-S. Liu, Tetrahedron Lett. 1997, 38, 7843; h) K. Manabe, S. Kobayashi, Org. Lett. 2003, 5, 3241. See also V. Michelet, M. Savignac, J. P. Genê, Electronic Encyclopedia of Reagents for Organic Synthesis, (Eds.: L. Paquette, P. Fuchs, D. Crich, P. Wipf), Wiley, New York, 2004.
19. The aqueous Tsuji-Trost reaction has been extensively investigated. For selected examples, see: a) M. Safi, D. Sinou, Tetrahedron Lett. 1991, 32, 2025; b) J. P. Genêt, E. Blart, M. Savignac, Synlett 1992, 715; c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, D. Sinou, Tetrahedron 1994, 50, 505; d) S. Kobayashi, W.W.-L. Lam, K. Manabe, Tetrahedron Lett. 2000, 41. 6115; e) H. Danjo, D. Tanaka, T. Hayashi, Y. Uozumi, Tetrahedron 1999, 55, 14341; f) Y. Uozumi, K. Shibatomi, J. Am. Chem. Soc. 2001, 123, 2919; g) D. E. Bergbreiter, Y.-S. Liu, Tetrahedron Lett. 1997, 38, 7843; h) K. Manabe, S. Kobayashi, Org. Lett. 2003, 5, 3241. See also V. Michelet, M. Savignac, J. P. Genê, Electronic Encyclopedia of Reagents for Organic Synthesis, (Eds.: L. Paquette, P. Fuchs, D. Crich, P. Wipf), Wiley, New York, 2004.
20. The aqueous Tsuji-Trost reaction has been extensively investigated. For selected examples, see: a) M. Safi, D. Sinou, Tetrahedron Lett. 1991, 32, 2025; b) J. P. Genêt, E. Blart, M. Savignac, Synlett 1992, 715; c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, D. Sinou, Tetrahedron 1994, 50, 505; d) S. Kobayashi, W.W.-L. Lam, K. Manabe, Tetrahedron Lett. 2000, 41. 6115; e) H. Danjo, D. Tanaka, T. Hayashi, Y. Uozumi, Tetrahedron 1999, 55, 14341; f) Y. Uozumi, K. Shibatomi, J. Am. Chem. Soc. 2001, 123, 2919; g) D. E. Bergbreiter, Y.-S. Liu, Tetrahedron Lett. 1997, 38, 7843; h) K. Manabe, S. Kobayashi, Org. Lett. 2003, 5, 3241. See also V. Michelet, M. Savignac, J. P. Genê, Electronic Encyclopedia of Reagents for Organic Synthesis, (Eds.: L. Paquette, P. Fuchs, D. Crich, P. Wipf), Wiley, New York, 2004.
21. The aqueous Tsuji-Trost reaction has been extensively investigated. For selected examples, see: a) M. Safi, D. Sinou, Tetrahedron Lett. 1991, 32, 2025; b) J. P. Genêt, E. Blart, M. Savignac, Synlett 1992, 715; c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, D. Sinou, Tetrahedron 1994, 50, 505; d) S. Kobayashi, W.W.-L. Lam, K. Manabe, Tetrahedron Lett. 2000, 41. 6115; e) H. Danjo, D. Tanaka, T. Hayashi, Y. Uozumi, Tetrahedron 1999, 55, 14341; f) Y. Uozumi, K. Shibatomi, J. Am. Chem. Soc. 2001, 123, 2919; g) D. E. Bergbreiter, Y.-S. Liu, Tetrahedron Lett. 1997, 38, 7843; h) K. Manabe, S. Kobayashi, Org. Lett. 2003, 5, 3241. See also V. Michelet, M. Savignac, J. P. Genê, Electronic Encyclopedia of Reagents for Organic Synthesis, (Eds.: L. Paquette, P. Fuchs, D. Crich, P. Wipf), Wiley, New York, 2004.
22. The aqueous Tsuji-Trost reaction has been extensively investigated. For selected examples, see: a) M. Safi, D. Sinou, Tetrahedron Lett. 1991, 32, 2025; b) J. P. Genêt, E. Blart, M. Savignac, Synlett 1992, 715; c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, D. Sinou, Tetrahedron 1994, 50, 505; d) S. Kobayashi, W.W.-L. Lam, K. Manabe, Tetrahedron Lett. 2000, 41. 6115; e) H. Danjo, D. Tanaka, T. Hayashi, Y. Uozumi, Tetrahedron 1999, 55, 14341; f) Y. Uozumi, K. Shibatomi, J. Am. Chem. Soc. 2001, 123, 2919; g) D. E. Bergbreiter, Y.-S. Liu, Tetrahedron Lett. 1997, 38, 7843; h) K. Manabe, S. Kobayashi, Org. Lett. 2003, 5, 3241. See also V. Michelet, M. Savignac, J. P. Genê, Electronic Encyclopedia of Reagents for Organic Synthesis, (Eds.: L. Paquette, P. Fuchs, D. Crich, P. Wipf), Wiley, New York, 2004.
23. The aqueous Tsuji-Trost reaction has been extensively investigated. For selected examples, see: a) M. Safi, D. Sinou, Tetrahedron Lett. 1991, 32, 2025; b) J. P. Genêt, E. Blart, M. Savignac, Synlett 1992, 715; c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, D. Sinou, Tetrahedron 1994, 50, 505; d) S. Kobayashi, W.W.-L. Lam, K. Manabe, Tetrahedron Lett. 2000, 41. 6115; e) H. Danjo, D. Tanaka, T. Hayashi, Y. Uozumi, Tetrahedron 1999, 55, 14341; f) Y. Uozumi, K. Shibatomi, J. Am. Chem. Soc. 2001, 123, 2919; g) D. E. Bergbreiter, Y.-S. Liu, Tetrahedron Lett. 1997, 38, 7843; h) K. Manabe, S. Kobayashi, Org. Lett. 2003, 5, 3241. See also V. Michelet, M. Savignac, J. P. Genê, Electronic Encyclopedia of Reagents for Organic Synthesis, (Eds.: L. Paquette, P. Fuchs, D. Crich, P. Wipf), Wiley, New York, 2004.
24. The aqueous Tsuji-Trost reaction has been extensively investigated. For selected examples, see: a) M. Safi, D. Sinou, Tetrahedron Lett. 1991, 32, 2025; b) J. P. Genêt, E. Blart, M. Savignac, Synlett 1992, 715; c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, D. Sinou, Tetrahedron 1994, 50, 505; d) S. Kobayashi, W.W.-L. Lam, K. Manabe, Tetrahedron Lett. 2000, 41. 6115; e) H. Danjo, D. Tanaka, T. Hayashi, Y. Uozumi, Tetrahedron 1999, 55, 14341; f) Y. Uozumi, K. Shibatomi, J. Am. Chem. Soc. 2001, 123, 2919; g) D. E. Bergbreiter, Y.-S. Liu, Tetrahedron Lett. 1997, 38, 7843; h) K. Manabe, S. Kobayashi, Org. Lett. 2003, 5, 3241. See also V. Michelet, M. Savignac, J. P. Genê, Electronic Encyclopedia of Reagents for Organic Synthesis, (Eds.: L. Paquette, P. Fuchs, D. Crich, P. Wipf), Wiley, New York, 2004.
25. The aqueous Tsuji-Trost reaction has been extensively investigated. For selected examples, see: a) M. Safi, D. Sinou, Tetrahedron Lett. 1991, 32, 2025; b) J. P. Genêt, E. Blart, M. Savignac, Synlett 1992, 715; c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, D. Sinou, Tetrahedron 1994, 50, 505; d) S. Kobayashi, W.W.-L. Lam, K. Manabe, Tetrahedron Lett. 2000, 41. 6115; e) H. Danjo, D. Tanaka, T. Hayashi, Y. Uozumi, Tetrahedron 1999, 55, 14341; f) Y. Uozumi, K. Shibatomi, J. Am. Chem. Soc. 2001, 123, 2919; g) D. E. Bergbreiter, Y.-S. Liu, Tetrahedron Lett. 1997, 38, 7843; h) K. Manabe, S. Kobayashi, Org. Lett. 2003, 5, 3241. See also V. Michelet, M. Savignac, J. P. Genê, Electronic Encyclopedia of Reagents for Organic Synthesis, (Eds.: L. Paquette, P. Fuchs, D. Crich, P. Wipf), Wiley, New York, 2004.
26. For the use of the Tsuji-Trost reaction for macrocyclization, see: a) B. M. Trost, Angew. Chem. 1989, 101, 1199; Angew. Chem. Int. Ed. Engl. 1989, 28, 1173; b) A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1998, 120, 2817; c) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2003, 125, 14722; d) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2004, 126, 11254; e) J. Pohlmann, C. Sabater, H. M. R. Hoffmann, Angew. Chem. 1998, 110, 656; Angew. Chem. Int. Ed. 1998, 37, 633.
27. For the use of the Tsuji-Trost reaction for macrocyclization, see: a) B. M. Trost, Angew. Chem. 1989, 101, 1199; Angew. Chem. Int. Ed. Engl. 1989, 28, 1173; b) A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1998, 120, 2817; c) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2003, 125, 14722; d) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2004, 126, 11254; e) J. Pohlmann, C. Sabater, H. M. R. Hoffmann, Angew. Chem. 1998, 110, 656; Angew. Chem. Int. Ed. 1998, 37, 633.
28. For the use of the Tsuji-Trost reaction for macrocyclization, see: a) B. M. Trost, Angew. Chem. 1989, 101, 1199; Angew. Chem. Int. Ed. Engl. 1989, 28, 1173; b) A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1998, 120, 2817; c) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2003, 125, 14722; d) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2004, 126, 11254; e) J. Pohlmann, C. Sabater, H. M. R. Hoffmann, Angew. Chem. 1998, 110, 656; Angew. Chem. Int. Ed. 1998, 37, 633.
29. For the use of the Tsuji-Trost reaction for macrocyclization, see: a) B. M. Trost, Angew. Chem. 1989, 101, 1199; Angew. Chem. Int. Ed. Engl. 1989, 28, 1173; b) A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1998, 120, 2817; c) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2003, 125, 14722; d) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2004, 126, 11254; e) J. Pohlmann, C. Sabater, H. M. R. Hoffmann, Angew. Chem. 1998, 110, 656; Angew. Chem. Int. Ed. 1998, 37, 633.
30. For the use of the Tsuji-Trost reaction for macrocyclization, see: a) B. M. Trost, Angew. Chem. 1989, 101, 1199; Angew. Chem. Int. Ed. Engl. 1989, 28, 1173; b) A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1998, 120, 2817; c) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2003, 125, 14722; d) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2004, 126, 11254; e) J. Pohlmann, C. Sabater, H. M. R. Hoffmann, Angew. Chem. 1998, 110, 656; Angew. Chem. Int. Ed. 1998, 37, 633.
31. For the use of the Tsuji-Trost reaction for macrocyclization, see: a) B. M. Trost, Angew. Chem. 1989, 101, 1199; Angew. Chem. Int. Ed. Engl. 1989, 28, 1173; b) A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1998, 120, 2817; c) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2003, 125, 14722; d) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2004, 126, 11254; e) J. Pohlmann, C. Sabater, H. M. R. Hoffmann, Angew. Chem. 1998, 110, 656; Angew. Chem. Int. Ed. 1998, 37, 633.
32. For the use of the Tsuji-Trost reaction for macrocyclization, see: a) B. M. Trost, Angew. Chem. 1989, 101, 1199; Angew. Chem. Int. Ed. Engl. 1989, 28, 1173; b) A. Fürstner, H. Weintritt, J. Am. Chem. Soc. 1998, 120, 2817; c) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2003, 125, 14722; d) R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K. Takao, K. Tadano, J. Am. Chem. Soc. 2004, 126, 11254; e) J. Pohlmann, C. Sabater, H. M. R. Hoffmann, Angew. Chem. 1998, 110, 656; Angew. Chem. Int. Ed. 1998, 37, 633.
33. 3 at room temperature and the starting material was recovered completely.
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36. The reaction in DMF with tri(o-tolyl)phosphine as the ligand provided none of the desired products 2 and 3.
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39. -1. This value equals 1.7% of the introduced substrate.