Asymmetric synthesis of chiral diols by the catalytic enantioselective dialkylation of tere-, iso-, and phthalaldehydes and by a catalytic enantioselective autoinductive reaction

Tetrahedron

Volumn 52, Issue 42, 1996, Pages 13355-13362

  Soai, Kenso ^a   Inoue, Yukikazu ^a   Takahashi, Tomohide ^a   Shibata, Takanori ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030583528     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00810-1     Document Type: Article

References (27)

1. 1. For a review: Whitesell, J. K. Chem. Rev. 1989, 89, 1581. See also, Johnson, W. S.; Harbet, C. A.; Ratcliffe, G. E.; Stipanovic, R. O. J. Am. Chem. Soc. 1976, 98, 6188; McNamura, J. M.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 7371; Sugimura, T.; Futagawa, T.; Yoshikawa, M.; Tai, A. Tetrahedron Lett. 1989, 30, 3807; Sugimura, T.; Futagawa, T.; Tai, A. Chem. Lett. 1990, 2291.
2. 1. For a review: Whitesell, J. K. Chem. Rev. 1989, 89, 1581. See also, Johnson, W. S.; Harbet, C. A.; Ratcliffe, G. E.; Stipanovic, R. O. J. Am. Chem. Soc. 1976, 98, 6188; McNamura, J. M.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 7371; Sugimura, T.; Futagawa, T.; Yoshikawa, M.; Tai, A. Tetrahedron Lett. 1989, 30, 3807; Sugimura, T.; Futagawa, T.; Tai, A. Chem. Lett. 1990, 2291.
3. 1. For a review: Whitesell, J. K. Chem. Rev. 1989, 89, 1581. See also, Johnson, W. S.; Harbet, C. A.; Ratcliffe, G. E.; Stipanovic, R. O. J. Am. Chem. Soc. 1976, 98, 6188; McNamura, J. M.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 7371; Sugimura, T.; Futagawa, T.; Yoshikawa, M.; Tai, A. Tetrahedron Lett. 1989, 30, 3807; Sugimura, T.; Futagawa, T.; Tai, A. Chem. Lett. 1990, 2291.
4. 1. For a review: Whitesell, J. K. Chem. Rev. 1989, 89, 1581. See also, Johnson, W. S.; Harbet, C. A.; Ratcliffe, G. E.; Stipanovic, R. O. J. Am. Chem. Soc. 1976, 98, 6188; McNamura, J. M.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 7371; Sugimura, T.; Futagawa, T.; Yoshikawa, M.; Tai, A. Tetrahedron Lett. 1989, 30, 3807; Sugimura, T.; Futagawa, T.; Tai, A. Chem. Lett. 1990, 2291.
5. 1. For a review: Whitesell, J. K. Chem. Rev. 1989, 89, 1581. See also, Johnson, W. S.; Harbet, C. A.; Ratcliffe, G. E.; Stipanovic, R. O. J. Am. Chem. Soc. 1976, 98, 6188; McNamura, J. M.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 7371; Sugimura, T.; Futagawa, T.; Yoshikawa, M.; Tai, A. Tetrahedron Lett. 1989, 30, 3807; Sugimura, T.; Futagawa, T.; Tai, A. Chem. Lett. 1990, 2291.
6. 2. Soai, K.; Hori, H.; Kawahara, M. J. Chem. Soc., Chem. Commun. 1992, 106.
7. 3. Alberts, A. M.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. The structures of the chiral catalyst (orthotitanate) and the product (Zn alkoxide, before quenching the reaction) are different, the reaction is not asymmetric autocatalytic. For other catalytic enantioselective autoinductive reaction, see ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1 1993, 885; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. For asymmetric autocatalytic reactions, see: Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982; Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry 1994, 5, 789; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry 1995, 6, 637; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751.
8. 3. Alberts, A. M.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. The structures of the chiral catalyst (orthotitanate) and the product (Zn alkoxide, before quenching the reaction) are different, the reaction is not asymmetric autocatalytic. For other catalytic enantioselective autoinductive reaction, see ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1 1993, 885; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. For asymmetric autocatalytic reactions, see: Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982; Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry 1994, 5, 789; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry 1995, 6, 637; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751.
9. 3. Alberts, A. M.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. The structures of the chiral catalyst (orthotitanate) and the product (Zn alkoxide, before quenching the reaction) are different, the reaction is not asymmetric autocatalytic. For other catalytic enantioselective autoinductive reaction, see ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1 1993, 885; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. For asymmetric autocatalytic reactions, see: Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982; Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry 1994, 5, 789; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry 1995, 6, 637; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751.
10. 3. Alberts, A. M.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. The structures of the chiral catalyst (orthotitanate) and the product (Zn alkoxide, before quenching the reaction) are different, the reaction is not asymmetric autocatalytic. For other catalytic enantioselective autoinductive reaction, see ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1 1993, 885; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. For asymmetric autocatalytic reactions, see: Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982; Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry 1994, 5, 789; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry 1995, 6, 637; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751.
11. 3. Alberts, A. M.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. The structures of the chiral catalyst (orthotitanate) and the product (Zn alkoxide, before quenching the reaction) are different, the reaction is not asymmetric autocatalytic. For other catalytic enantioselective autoinductive reaction, see ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1 1993, 885; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. For asymmetric autocatalytic reactions, see: Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982; Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry 1994, 5, 789; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry 1995, 6, 637; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751.
12. 3. Alberts, A. M.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. The structures of the chiral catalyst (orthotitanate) and the product (Zn alkoxide, before quenching the reaction) are different, the reaction is not asymmetric autocatalytic. For other catalytic enantioselective autoinductive reaction, see ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1 1993, 885; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. For asymmetric autocatalytic reactions, see: Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982; Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry 1994, 5, 789; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry 1995, 6, 637; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751.
13. 3. Alberts, A. M.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. The structures of the chiral catalyst (orthotitanate) and the product (Zn alkoxide, before quenching the reaction) are different, the reaction is not asymmetric autocatalytic. For other catalytic enantioselective autoinductive reaction, see ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1 1993, 885; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. For asymmetric autocatalytic reactions, see: Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982; Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry 1994, 5, 789; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry 1995, 6, 637; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751.
14. 3. Alberts, A. M.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. The structures of the chiral catalyst (orthotitanate) and the product (Zn alkoxide, before quenching the reaction) are different, the reaction is not asymmetric autocatalytic. For other catalytic enantioselective autoinductive reaction, see ShengJian, L.; Yaozhong, J.; Aiqiao, M.; Guishu, Y. J. Chem. Soc., Perkin Trans. 1 1993, 885; Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. For asymmetric autocatalytic reactions, see: Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982; Soai, K.; Hayase, T.; Shimada, C.; Isobe, K. Tetrahedron: Asymmetry 1994, 5, 789; Soai, K.; Hayase, T.; Takai, K. Tetrahedron: Asymmetry 1995, 6, 637; Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471; Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751.
15. 4. Review by us: Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833; Soai, K.; Hayase, T. Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.) 1995, 53, 138; review by others: Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
16. 4. Review by us: Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833; Soai, K.; Hayase, T. Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.) 1995, 53, 138; review by others: Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
17. 4. Review by us: Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833; Soai, K.; Hayase, T. Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.) 1995, 53, 138; review by others: Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
18. 5. Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690; Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264; Soai, K.; Hayasaka, T.; Takai, K.; Sugiyama, T. J. Org. Chem. 1994, 59, 7908.
19. 5. Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690; Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264; Soai, K.; Hayasaka, T.; Takai, K.; Sugiyama, T. J. Org. Chem. 1994, 59, 7908.
20. 5. Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690; Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264; Soai, K.; Hayasaka, T.; Takai, K.; Sugiyama, T. J. Org. Chem. 1994, 59, 7908.
21. 6. Soai, K.; Hirose, Y.; Ohno, Y. Tetrahedron: Asymmetry 1993, 4, 1473; Soai, K.; Ohno, Y.; Inoue, Y.; Tsuruoka, T.; Hirose, Y. Recl. Trav. Chim. Pays-Bas. 1995, 114, 145.
22. 6. Soai, K.; Hirose, Y.; Ohno, Y. Tetrahedron: Asymmetry 1993, 4, 1473; Soai, K.; Ohno, Y.; Inoue, Y.; Tsuruoka, T.; Hirose, Y. Recl. Trav. Chim. Pays-Bas. 1995, 114, 145.
23. 7. For the chiral titanium complex catalyzed alkylation, (a) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691;
24. (b) Rozema, M. J.; Sidduri, A.; Knochel, P. J. Org. Chem. 1992, 57, 1956;
25. (c) Soai, K.; Hirose Y.; Ohno, Y.; Tetrahedron: Asymmetry 1993, 4, 1473;
26. (d) For an asymmetric synthesis of diols, Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363.
27. 8. Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742.