Tunable C2-Chiral 1,2-Diols. Syntheses of 1,4-Bis-Alkoxybutane-2S,3S-diols

Synlett

Volumn 1996, Issue 1, 1996, Pages 53-54

  Yuan, Tien Min ^a   Hsieh, Yu Tsai ^a   Yeh, Sue Min ^a   Shyue, Jing Jong ^a   Luh, Tien Yau ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542715342     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5329     Document Type: Article

References (24)

1. Noyori, R. Asymmetric Catalysis in Organic Synthesis;Wiley: New York, 1994;
2. For recent reviews, see: (a) Weidmann, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1983, 22, 31; (b) Braun, M. Angew. Chem. Int. Ed. Engl. 1987, 26, 24; (c) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49; (d) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807; (e) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
3. For recent reviews, see: (a) Weidmann, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1983, 22, 31; (b) Braun, M. Angew. Chem. Int. Ed. Engl. 1987, 26, 24; (c) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49; (d) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807; (e) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
4. For recent reviews, see: (a) Weidmann, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1983, 22, 31; (b) Braun, M. Angew. Chem. Int. Ed. Engl. 1987, 26, 24; (c) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49; (d) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807; (e) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
5. For recent reviews, see: (a) Weidmann, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1983, 22, 31; (b) Braun, M. Angew. Chem. Int. Ed. Engl. 1987, 26, 24; (c) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49; (d) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807; (e) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
6. For recent reviews, see: (a) Weidmann, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1983, 22, 31; (b) Braun, M. Angew. Chem. Int. Ed. Engl. 1987, 26, 24; (c) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49; (d) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807; (e) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
7. For examples: (a) Weber, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1992, 31, 84; (b) Corey, E. J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289; (c) Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Nihata, S. J. Am. Chem. Soc. 1992, 114, 8869; (d) Maruoka, K.; Banno, H.; Yamamoto, H. ibid. 1990, 112, 7791; (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; (f) Bao, J.; Wullf, W. D. J. Am. Chem. Soc. . 1993, 115, 3814;
8. For examples: (a) Weber, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1992, 31, 84; (b) Corey, E. J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289; (c) Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Nihata, S. J. Am. Chem. Soc. 1992, 114, 8869; (d) Maruoka, K.; Banno, H.; Yamamoto, H. ibid. 1990, 112, 7791; (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; (f) Bao, J.; Wullf, W. D. J. Am. Chem. Soc. . 1993, 115, 3814;
9. For examples: (a) Weber, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1992, 31, 84; (b) Corey, E. J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289; (c) Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Nihata, S. J. Am. Chem. Soc. 1992, 114, 8869; (d) Maruoka, K.; Banno, H.; Yamamoto, H. ibid. 1990, 112, 7791; (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; (f) Bao, J.; Wullf, W. D. J. Am. Chem. Soc. . 1993, 115, 3814;
10. For examples: (a) Weber, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1992, 31, 84; (b) Corey, E. J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289; (c) Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Nihata, S. J. Am. Chem. Soc. 1992, 114, 8869; (d) Maruoka, K.; Banno, H.; Yamamoto, H. ibid. 1990, 112, 7791; (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; (f) Bao, J.; Wullf, W. D. J. Am. Chem. Soc. . 1993, 115, 3814;
11. For examples: (a) Weber, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1992, 31, 84; (b) Corey, E. J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289; (c) Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Nihata, S. J. Am. Chem. Soc. 1992, 114, 8869; (d) Maruoka, K.; Banno, H.; Yamamoto, H. ibid. 1990, 112, 7791; (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; (f) Bao, J.; Wullf, W. D. J. Am. Chem. Soc. . 1993, 115, 3814;
12. For examples: (a) Weber, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1992, 31, 84; (b) Corey, E. J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289; (c) Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Nihata, S. J. Am. Chem. Soc. 1992, 114, 8869; (d) Maruoka, K.; Banno, H.; Yamamoto, H. ibid. 1990, 112, 7791; (e) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; (f) Bao, J.; Wullf, W. D. J. Am. Chem. Soc. . 1993, 115, 3814;
13. (a) Cheng, W.-L.; Yeh, S.-M.; Luh, T.-Y. J. Org. Chem. 1993, 55, 5576.
14. (b) Chen, Y.-H.; Luh, T.-Y.; Lee, G.-H.; Peng, S.-M. J. Chem. Soc., Chem. Commun. 1994, 2369.
15. Mash, E. A.; Nelson, K. A.; Van Deusen, S.; Hemperly, S. B. Org. Syn. 1989, 68, 92.
16. 3, 75 MHz) δ 22.1, 24.6, 25.6, 36.2, 36.3, 62.9, 71.0, 74.0.
17. (a) Eliel, E. L.; Badding, V. G.; Rerick, M. N. J. Am. Chem. Soc. 1962, 84, 2371.
18. (b) Eliel, E. L.; Newak, B. E.; Daignault, R. A.; Badding, V. G. J. Org. Chem. 1965, 30, 2441; Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83; Yamamoto, K.; Ando, H.; Chikamatsu, H. J. Chem. Soc. Chem. Commun. 1987, 334.
19. (b) Eliel, E. L.; Newak, B. E.; Daignault, R. A.; Badding, V. G. J. Org. Chem. 1965, 30, 2441; Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83; Yamamoto, K.; Ando, H.; Chikamatsu, H. J. Chem. Soc. Chem. Commun. 1987, 334.
20. (b) Eliel, E. L.; Newak, B. E.; Daignault, R. A.; Badding, V. G. J. Org. Chem. 1965, 30, 2441; Mori, A.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Organomet. Chem. 1985, 285, 83; Yamamoto, K.; Ando, H.; Chikamatsu, H. J. Chem. Soc. Chem. Commun. 1987, 334.
21. Eisch, J. J. In Comprehensive Organometallic Chemistry, Wilkinson, G.; Stone, F. G. A.; Abel, E. W. Eds., Pergamon: Oxford, 1982, Vol 1, p. 555.
22. Aluminum reagent-promoted regioselective alkylative ring opening of an acetal having a neighboring hydroxy group (but not an alkoxy group) has been reported. (Cf. Takano, S.; Ohkawa, T.; Ogasawara, K. Tetrahedron Lett. 1988, 29, 1823.)
23. 3, 75 MHz) δ 17.7, 17.8, 18.5, 18.7, 20.1, 20.2, 20.3, 20.4, 30.1, 30.5, 30.6, 30.7, 61.7, 71.9, 74.0, 79.1, 87.4, 91.7.
24. Yeh, S.-M.;-Huang, L.-S.; Luh, T.-Y. submitted for publication.