Thiacrown Ether Technology in Lipase-Catalyzed Reaction: Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

Journal of Organic Chemistry

Volumn 62, Issue 26, 1997, Pages 9165-9172

  Itoh, Toshiyuki ^a   Mitsukura, Koichi ^a   Kanphai, Wipa ^a   Takagi, Yumiko ^b   Kihara, Hiroshi ^b   Tsukube, Hiroshi ^c  

^a OKAYAMA UNIVERSITY   (Japan)

^b HYOGO UNIVERSITY OF TEACHER EDUCATION   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000377492     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971288m     Document Type: Article

References (38)

1. For preliminary accounts for crown ether-modified lipase-catalyzed reactions, see: (a) Itoh, T.; Takagi, Y.; Murakami, T.; Hiyama, Y.; Tsukube, H. J. Org. Chem. 1996, 61, 2158. (b) Itoh, T.; Hiyama, Y.; Betchaku, A.; Tsukube, H. Tetrahedron Lett. 1993, 34, 2617. (c) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991. (d) Itoh, T.; Mitsukura, K.; Kaihatsu, K.; Hamada, H.; Takagi, Y.; Tsukube, H. J. Chem. Soc., Perkin Trans. 1 1997, 2275.
2. For preliminary accounts for crown ether-modified lipase-catalyzed reactions, see: (a) Itoh, T.; Takagi, Y.; Murakami, T.; Hiyama, Y.; Tsukube, H. J. Org. Chem. 1996, 61, 2158. (b) Itoh, T.; Hiyama, Y.; Betchaku, A.; Tsukube, H. Tetrahedron Lett. 1993, 34, 2617. (c) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991. (d) Itoh, T.; Mitsukura, K.; Kaihatsu, K.; Hamada, H.; Takagi, Y.; Tsukube, H. J. Chem. Soc., Perkin Trans. 1 1997, 2275.
3. For preliminary accounts for crown ether-modified lipase-catalyzed reactions, see: (a) Itoh, T.; Takagi, Y.; Murakami, T.; Hiyama, Y.; Tsukube, H. J. Org. Chem. 1996, 61, 2158. (b) Itoh, T.; Hiyama, Y.; Betchaku, A.; Tsukube, H. Tetrahedron Lett. 1993, 34, 2617. (c) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991. (d) Itoh, T.; Mitsukura, K.; Kaihatsu, K.; Hamada, H.; Takagi, Y.; Tsukube, H. J. Chem. Soc., Perkin Trans. 1 1997, 2275.
4. For preliminary accounts for crown ether-modified lipase-catalyzed reactions, see: (a) Itoh, T.; Takagi, Y.; Murakami, T.; Hiyama, Y.; Tsukube, H. J. Org. Chem. 1996, 61, 2158. (b) Itoh, T.; Hiyama, Y.; Betchaku, A.; Tsukube, H. Tetrahedron Lett. 1993, 34, 2617. (c) Takagi, Y.; Teramoto, J.; Kihara, H.; Itoh, T.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991. (d) Itoh, T.; Mitsukura, K.; Kaihatsu, K.; Hamada, H.; Takagi, Y.; Tsukube, H. J. Chem. Soc., Perkin Trans. 1 1997, 2275.
5. Reviews: (a) Wong C. H.; Whitesides, G. M. In Enzymes in Synthetic Organic Chemistry; Baldwin, J. E., Magnus, P. D., Eds.; Tetrahedron Organic Chemistry Series Vol. 12; Pergamon: New York, 1994. (b) Klivanov, A. M. Acc. Chem. Res. 1990, 23, 114. (c) Janssen, J. M.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1991, 47, 7645. (d) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem., Jpn. 1995, 53, 668. (e) Theil, F. Chem. Rev. 1995, 95, 2203.
6. Reviews: (a) Wong C. H.; Whitesides, G. M. In Enzymes in Synthetic Organic Chemistry; Baldwin, J. E., Magnus, P. D., Eds.; Tetrahedron Organic Chemistry Series Vol. 12; Pergamon: New York, 1994. (b) Klivanov, A. M. Acc. Chem. Res. 1990, 23, 114. (c) Janssen, J. M.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1991, 47, 7645. (d) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem., Jpn. 1995, 53, 668. (e) Theil, F. Chem. Rev. 1995, 95, 2203.
7. Reviews: (a) Wong C. H.; Whitesides, G. M. In Enzymes in Synthetic Organic Chemistry; Baldwin, J. E., Magnus, P. D., Eds.; Tetrahedron Organic Chemistry Series Vol. 12; Pergamon: New York, 1994. (b) Klivanov, A. M. Acc. Chem. Res. 1990, 23, 114. (c) Janssen, J. M.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1991, 47, 7645. (d) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem., Jpn. 1995, 53, 668. (e) Theil, F. Chem. Rev. 1995, 95, 2203.
8. Reviews: (a) Wong C. H.; Whitesides, G. M. In Enzymes in Synthetic Organic Chemistry; Baldwin, J. E., Magnus, P. D., Eds.; Tetrahedron Organic Chemistry Series Vol. 12; Pergamon: New York, 1994. (b) Klivanov, A. M. Acc. Chem. Res. 1990, 23, 114. (c) Janssen, J. M.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1991, 47, 7645. (d) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem., Jpn. 1995, 53, 668. (e) Theil, F. Chem. Rev. 1995, 95, 2203.
9. Reviews: (a) Wong C. H.; Whitesides, G. M. In Enzymes in Synthetic Organic Chemistry; Baldwin, J. E., Magnus, P. D., Eds.; Tetrahedron Organic Chemistry Series Vol. 12; Pergamon: New York, 1994. (b) Klivanov, A. M. Acc. Chem. Res. 1990, 23, 114. (c) Janssen, J. M.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1991, 47, 7645. (d) Nakamura, K.; Hirose, Y. J. Synth. Org. Chem., Jpn. 1995, 53, 668. (e) Theil, F. Chem. Rev. 1995, 95, 2203.
10. Itoh, T.; Takagi, Y.; Tsukube, H. Trends Org. Chem. 1997, 6, 1.
11. For example, see: (a) Itoh, T.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1991, 56, 1521. (b) Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. Tetrahedron: Asymm. 1996, 7, 625 and references therein.
12. For example, see: (a) Itoh, T.; Takagi, Y.; Nishiyama, S. J. Org. Chem. 1991, 56, 1521. (b) Ema, T.; Maeno, S.; Takaya, Y.; Sakai, T.; Utaka, M. Tetrahedron: Asymm. 1996, 7, 625 and references therein.
13. Review see: (a) Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1993, 1206, 1. (b) Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 63.
14. Review see: (a) Wescott, C. R.; Klibanov, A. M. Biochim. Biophys. Acta 1993, 1206, 1. (b) Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 63.
15. 6h) were reported to be effective. (a) Guo, Z.-W.; Sih, C. J. J. Am. Chem. Soc. 1989, 111, 6839. (b) Itoh, T.; Ohira, E.; Takagi, Y.; Nishiyama, S.; Nakamura, K. Bull. Chem. Soc. Jpn. 1991, 64, 624. (c) Tsukube, H.; Betchaku, A.; Hiyama, Y.; Itoh, T. J. Chem. Soc., Chem. Commun. 1992, 1751. (d) Holmberg, E.; Holmquist, M.; Hedenstrom, E.; Berglund, P.; Norin, T.; Hogberg, H.-E.; Hult, K. Appl. Microbiol. Biotechnol. 1992, 35, 572. (e) Khmelnitsky, Y. L.; Welch, S. H.; Clark, D. S.; Dordick, J. S. J. Am. Chem. Soc. 1994, 116, 2647. (f) Tsukube, H.; Hiyama, Y.; Betchaku, A.; Itoh, T. J. Org. Chem. 1994, 59, 7014. (g) Bhaskar, R. A.; Rehman, H.; Krishnakumari, B.; Yadav, J. S. Tetrahedron Lett. 1994, 35, 2611. (h) Nagao, Y.; Tohjo, T.; Kaneuchi, T.; Yukimoto, Y.; Kume, M. Chem. Lett. 1992, 1817.
16. 6h) were reported to be effective. (a) Guo, Z.-W.; Sih, C. J. J. Am. Chem. Soc. 1989, 111, 6839. (b) Itoh, T.; Ohira, E.; Takagi, Y.; Nishiyama, S.; Nakamura, K. Bull. Chem. Soc. Jpn. 1991, 64, 624. (c) Tsukube, H.; Betchaku, A.; Hiyama, Y.; Itoh, T. J. Chem. Soc., Chem. Commun. 1992, 1751. (d) Holmberg, E.; Holmquist, M.; Hedenstrom, E.; Berglund, P.; Norin, T.; Hogberg, H.-E.; Hult, K. Appl. Microbiol. Biotechnol. 1992, 35, 572. (e) Khmelnitsky, Y. L.; Welch, S. H.; Clark, D. S.; Dordick, J. S. J. Am. Chem. Soc. 1994, 116, 2647. (f) Tsukube, H.; Hiyama, Y.; Betchaku, A.; Itoh, T. J. Org. Chem. 1994, 59, 7014. (g) Bhaskar, R. A.; Rehman, H.; Krishnakumari, B.; Yadav, J. S. Tetrahedron Lett. 1994, 35, 2611. (h) Nagao, Y.; Tohjo, T.; Kaneuchi, T.; Yukimoto, Y.; Kume, M. Chem. Lett. 1992, 1817.
17. 6h) were reported to be effective. (a) Guo, Z.-W.; Sih, C. J. J. Am. Chem. Soc. 1989, 111, 6839. (b) Itoh, T.; Ohira, E.; Takagi, Y.; Nishiyama, S.; Nakamura, K. Bull. Chem. Soc. Jpn. 1991, 64, 624. (c) Tsukube, H.; Betchaku, A.; Hiyama, Y.; Itoh, T. J. Chem. Soc., Chem. Commun. 1992, 1751. (d) Holmberg, E.; Holmquist, M.; Hedenstrom, E.; Berglund, P.; Norin, T.; Hogberg, H.-E.; Hult, K. Appl. Microbiol. Biotechnol. 1992, 35, 572. (e) Khmelnitsky, Y. L.; Welch, S. H.; Clark, D. S.; Dordick, J. S. J. Am. Chem. Soc. 1994, 116, 2647. (f) Tsukube, H.; Hiyama, Y.; Betchaku, A.; Itoh, T. J. Org. Chem. 1994, 59, 7014. (g) Bhaskar, R. A.; Rehman, H.; Krishnakumari, B.; Yadav, J. S. Tetrahedron Lett. 1994, 35, 2611. (h) Nagao, Y.; Tohjo, T.; Kaneuchi, T.; Yukimoto, Y.; Kume, M. Chem. Lett. 1992, 1817.
18. 6h) were reported to be effective. (a) Guo, Z.-W.; Sih, C. J. J. Am. Chem. Soc. 1989, 111, 6839. (b) Itoh, T.; Ohira, E.; Takagi, Y.; Nishiyama, S.; Nakamura, K. Bull. Chem. Soc. Jpn. 1991, 64, 624. (c) Tsukube, H.; Betchaku, A.; Hiyama, Y.; Itoh, T. J. Chem. Soc., Chem. Commun. 1992, 1751. (d) Holmberg, E.; Holmquist, M.; Hedenstrom, E.; Berglund, P.; Norin, T.; Hogberg, H.-E.; Hult, K. Appl. Microbiol. Biotechnol. 1992, 35, 572. (e) Khmelnitsky, Y. L.; Welch, S. H.; Clark, D. S.; Dordick, J. S. J. Am. Chem. Soc. 1994, 116, 2647. (f) Tsukube, H.; Hiyama, Y.; Betchaku, A.; Itoh, T. J. Org. Chem. 1994, 59, 7014. (g) Bhaskar, R. A.; Rehman, H.; Krishnakumari, B.; Yadav, J. S. Tetrahedron Lett. 1994, 35, 2611. (h) Nagao, Y.; Tohjo, T.; Kaneuchi, T.; Yukimoto, Y.; Kume, M. Chem. Lett. 1992, 1817.
19. 6h) were reported to be effective. (a) Guo, Z.-W.; Sih, C. J. J. Am. Chem. Soc. 1989, 111, 6839. (b) Itoh, T.; Ohira, E.; Takagi, Y.; Nishiyama, S.; Nakamura, K. Bull. Chem. Soc. Jpn. 1991, 64, 624. (c) Tsukube, H.; Betchaku, A.; Hiyama, Y.; Itoh, T. J. Chem. Soc., Chem. Commun. 1992, 1751. (d) Holmberg, E.; Holmquist, M.; Hedenstrom, E.; Berglund, P.; Norin, T.; Hogberg, H.-E.; Hult, K. Appl. Microbiol. Biotechnol. 1992, 35, 572. (e) Khmelnitsky, Y. L.; Welch, S. H.; Clark, D. S.; Dordick, J. S. J. Am. Chem. Soc. 1994, 116, 2647. (f) Tsukube, H.; Hiyama, Y.; Betchaku, A.; Itoh, T. J. Org. Chem. 1994, 59, 7014. (g) Bhaskar, R. A.; Rehman, H.; Krishnakumari, B.; Yadav, J. S. Tetrahedron Lett. 1994, 35, 2611. (h) Nagao, Y.; Tohjo, T.; Kaneuchi, T.; Yukimoto, Y.; Kume, M. Chem. Lett. 1992, 1817.
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