A practical route to enantiopure 1,2-aminoalcohols

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3219-3222

  Chang, Han Ting ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029937757     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00534-5     Document Type: Article

References (27)

1. Butsugan, Y.; Araki, S.; Watanabe, M. Ferrocenes ; VCH: Weinheim, 1995, 143-169; Tanaka, K. Yuki Gosei Kagaku Kyokaishi 1993, 51, 620; Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547; Shioiri, Y.; Hamada, Y. Heterocycles 1988, 27, 1035; Rousch, W. R.; Hawkins, J. M.; Grubbs, R. H. Chemtracts: Org. Chem. 1988, 1, 21; Itsuno, S. Yuki Gosei Kagaku Kyokaishi 1987, 45, 101; Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103; Barlow, C. B.; Bukhari, S. T.; Guthrie, R. D.; Prior, A. M. Asymmetry Carbohydr.; Dekker; New York, 1979, 81-99.
2. Butsugan, Y.; Araki, S.; Watanabe, M. Ferrocenes ; VCH: Weinheim, 1995, 143-169; Tanaka, K. Yuki Gosei Kagaku Kyokaishi 1993, 51, 620; Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547; Shioiri, Y.; Hamada, Y. Heterocycles 1988, 27, 1035; Rousch, W. R.; Hawkins, J. M.; Grubbs, R. H. Chemtracts: Org. Chem. 1988, 1, 21; Itsuno, S. Yuki Gosei Kagaku Kyokaishi 1987, 45, 101; Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103; Barlow, C. B.; Bukhari, S. T.; Guthrie, R. D.; Prior, A. M. Asymmetry Carbohydr.; Dekker; New York, 1979, 81-99.
3. Butsugan, Y.; Araki, S.; Watanabe, M. Ferrocenes ; VCH: Weinheim, 1995, 143-169; Tanaka, K. Yuki Gosei Kagaku Kyokaishi 1993, 51, 620; Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547; Shioiri, Y.; Hamada, Y. Heterocycles 1988, 27, 1035; Rousch, W. R.; Hawkins, J. M.; Grubbs, R. H. Chemtracts: Org. Chem. 1988, 1, 21; Itsuno, S. Yuki Gosei Kagaku Kyokaishi 1987, 45, 101; Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103; Barlow, C. B.; Bukhari, S. T.; Guthrie, R. D.; Prior, A. M. Asymmetry Carbohydr.; Dekker; New York, 1979, 81-99.
4. Butsugan, Y.; Araki, S.; Watanabe, M. Ferrocenes ; VCH: Weinheim, 1995, 143-169; Tanaka, K. Yuki Gosei Kagaku Kyokaishi 1993, 51, 620; Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547; Shioiri, Y.; Hamada, Y. Heterocycles 1988, 27, 1035; Rousch, W. R.; Hawkins, J. M.; Grubbs, R. H. Chemtracts: Org. Chem. 1988, 1, 21; Itsuno, S. Yuki Gosei Kagaku Kyokaishi 1987, 45, 101; Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103; Barlow, C. B.; Bukhari, S. T.; Guthrie, R. D.; Prior, A. M. Asymmetry Carbohydr.; Dekker; New York, 1979, 81-99.
5. Butsugan, Y.; Araki, S.; Watanabe, M. Ferrocenes ; VCH: Weinheim, 1995, 143-169; Tanaka, K. Yuki Gosei Kagaku Kyokaishi 1993, 51, 620; Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547; Shioiri, Y.; Hamada, Y. Heterocycles 1988, 27, 1035; Rousch, W. R.; Hawkins, J. M.; Grubbs, R. H. Chemtracts: Org. Chem. 1988, 1, 21; Itsuno, S. Yuki Gosei Kagaku Kyokaishi 1987, 45, 101; Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103; Barlow, C. B.; Bukhari, S. T.; Guthrie, R. D.; Prior, A. M. Asymmetry Carbohydr.; Dekker; New York, 1979, 81-99.
6. Butsugan, Y.; Araki, S.; Watanabe, M. Ferrocenes ; VCH: Weinheim, 1995, 143-169; Tanaka, K. Yuki Gosei Kagaku Kyokaishi 1993, 51, 620; Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547; Shioiri, Y.; Hamada, Y. Heterocycles 1988, 27, 1035; Rousch, W. R.; Hawkins, J. M.; Grubbs, R. H. Chemtracts: Org. Chem. 1988, 1, 21; Itsuno, S. Yuki Gosei Kagaku Kyokaishi 1987, 45, 101; Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103; Barlow, C. B.; Bukhari, S. T.; Guthrie, R. D.; Prior, A. M. Asymmetry Carbohydr.; Dekker; New York, 1979, 81-99.
7. Butsugan, Y.; Araki, S.; Watanabe, M. Ferrocenes ; VCH: Weinheim, 1995, 143-169; Tanaka, K. Yuki Gosei Kagaku Kyokaishi 1993, 51, 620; Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547; Shioiri, Y.; Hamada, Y. Heterocycles 1988, 27, 1035; Rousch, W. R.; Hawkins, J. M.; Grubbs, R. H. Chemtracts: Org. Chem. 1988, 1, 21; Itsuno, S. Yuki Gosei Kagaku Kyokaishi 1987, 45, 101; Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103; Barlow, C. B.; Bukhari, S. T.; Guthrie, R. D.; Prior, A. M. Asymmetry Carbohydr.; Dekker; New York, 1979, 81-99.
8. Butsugan, Y.; Araki, S.; Watanabe, M. Ferrocenes ; VCH: Weinheim, 1995, 143-169; Tanaka, K. Yuki Gosei Kagaku Kyokaishi 1993, 51, 620; Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547; Shioiri, Y.; Hamada, Y. Heterocycles 1988, 27, 1035; Rousch, W. R.; Hawkins, J. M.; Grubbs, R. H. Chemtracts: Org. Chem. 1988, 1, 21; Itsuno, S. Yuki Gosei Kagaku Kyokaishi 1987, 45, 101; Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103; Barlow, C. B.; Bukhari, S. T.; Guthrie, R. D.; Prior, A. M. Asymmetry Carbohydr.; Dekker; New York, 1979, 81-99.
9. Ishizuka, T.; Kunieda, T. Yakugaku Zasshi 1995, 115, 460; Kunieda, T.; Ishizuka, T. Stud. Nat. Prod. Chem. 1993, 12, 411; Ganesan, A.; Heathcock, C. H. Chemtracts: Org. Chem. 1988, 1, 317; Martin, C. A.; Sharpless, K. B. Chemtracts: Org. Chem. 1988, 1, 165; Narasaka, K. Kagaku, 1985, 40, 756; Tramontini, M. Synthesis 1982, 8, 605.
10. Ishizuka, T.; Kunieda, T. Yakugaku Zasshi 1995, 115, 460; Kunieda, T.; Ishizuka, T. Stud. Nat. Prod. Chem. 1993, 12, 411; Ganesan, A.; Heathcock, C. H. Chemtracts: Org. Chem. 1988, 1, 317; Martin, C. A.; Sharpless, K. B. Chemtracts: Org. Chem. 1988, 1, 165; Narasaka, K. Kagaku, 1985, 40, 756; Tramontini, M. Synthesis 1982, 8, 605.
11. Ishizuka, T.; Kunieda, T. Yakugaku Zasshi 1995, 115, 460; Kunieda, T.; Ishizuka, T. Stud. Nat. Prod. Chem. 1993, 12, 411; Ganesan, A.; Heathcock, C. H. Chemtracts: Org. Chem. 1988, 1, 317; Martin, C. A.; Sharpless, K. B. Chemtracts: Org. Chem. 1988, 1, 165; Narasaka, K. Kagaku, 1985, 40, 756; Tramontini, M. Synthesis 1982, 8, 605.
12. Ishizuka, T.; Kunieda, T. Yakugaku Zasshi 1995, 115, 460; Kunieda, T.; Ishizuka, T. Stud. Nat. Prod. Chem. 1993, 12, 411; Ganesan, A.; Heathcock, C. H. Chemtracts: Org. Chem. 1988, 1, 317; Martin, C. A.; Sharpless, K. B. Chemtracts: Org. Chem. 1988, 1, 165; Narasaka, K. Kagaku, 1985, 40, 756; Tramontini, M. Synthesis 1982, 8, 605.
13. Ishizuka, T.; Kunieda, T. Yakugaku Zasshi 1995, 115, 460; Kunieda, T.; Ishizuka, T. Stud. Nat. Prod. Chem. 1993, 12, 411; Ganesan, A.; Heathcock, C. H. Chemtracts: Org. Chem. 1988, 1, 317; Martin, C. A.; Sharpless, K. B. Chemtracts: Org. Chem. 1988, 1, 165; Narasaka, K. Kagaku, 1985, 40, 756; Tramontini, M. Synthesis 1982, 8, 605.
14. Ishizuka, T.; Kunieda, T. Yakugaku Zasshi 1995, 115, 460; Kunieda, T.; Ishizuka, T. Stud. Nat. Prod. Chem. 1993, 12, 411; Ganesan, A.; Heathcock, C. H. Chemtracts: Org. Chem. 1988, 1, 317; Martin, C. A.; Sharpless, K. B. Chemtracts: Org. Chem. 1988, 1, 165; Narasaka, K. Kagaku, 1985, 40, 756; Tramontini, M. Synthesis 1982, 8, 605.
15. Wang, Z. M.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302; Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
16. Wang, Z. M.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302; Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
17. Hampton, A.; Nichol, A. W. Biochemistry 1966, 5, 2076; Cunningham, J.; Gigg, R. J. Chem. Soc. 1965, 1553.
18. Hampton, A.; Nichol, A. W. Biochemistry 1966, 5, 2076; Cunningham, J.; Gigg, R. J. Chem. Soc. 1965, 1553.
19. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley & Sons: New York, 1991.
20. Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Jang, S.-B. Tetrahedron Lett. 1995, 36, 8047; Kang, S.-K.; Park, D.-C.; Jeon, J.-H.; Rho, H.-S.; Yu, C.-M. Tetrahedron Lett. 1994, 35, 2357; Kang, S.-K.; Park, D.-C.; Rho, H.-S.; Yoon, S.-H.; Shin, J.-S. J. Chem. Soc., Perkin Trans. 1 1994, 3513; Inoue, Y.; Matsushita, K.; Yen, I-F.; Imaizumi, S. Chem. Lett. 1991, 1377.
21. Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Jang, S.-B. Tetrahedron Lett. 1995, 36, 8047; Kang, S.-K.; Park, D.-C.; Jeon, J.-H.; Rho, H.-S.; Yu, C.-M. Tetrahedron Lett. 1994, 35, 2357; Kang, S.-K.; Park, D.-C.; Rho, H.-S.; Yoon, S.-H.; Shin, J.-S. J. Chem. Soc., Perkin Trans. 1 1994, 3513; Inoue, Y.; Matsushita, K.; Yen, I-F.; Imaizumi, S. Chem. Lett. 1991, 1377.
22. Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Jang, S.-B. Tetrahedron Lett. 1995, 36, 8047; Kang, S.-K.; Park, D.-C.; Jeon, J.-H.; Rho, H.-S.; Yu, C.-M. Tetrahedron Lett. 1994, 35, 2357; Kang, S.-K.; Park, D.-C.; Rho, H.-S.; Yoon, S.-H.; Shin, J.-S. J. Chem. Soc., Perkin Trans. 1 1994, 3513; Inoue, Y.; Matsushita, K.; Yen, I-F.; Imaizumi, S. Chem. Lett. 1991, 1377.
23. Kang, S.-K.; Jung, K.-Y.; Park, C.-H.; Jang, S.-B. Tetrahedron Lett. 1995, 36, 8047; Kang, S.-K.; Park, D.-C.; Jeon, J.-H.; Rho, H.-S.; Yu, C.-M. Tetrahedron Lett. 1994, 35, 2357; Kang, S.-K.; Park, D.-C.; Rho, H.-S.; Yoon, S.-H.; Shin, J.-S. J. Chem. Soc., Perkin Trans. 1 1994, 3513; Inoue, Y.; Matsushita, K.; Yen, I-F.; Imaizumi, S. Chem. Lett. 1991, 1377.
24. Cama, L. D.; Leanza, W. J.; Beattie, T. R.; Christensen, B. G. J. Am. Chem. Soc. 1972, 94, 1408; Moore, A. T.; Rydon, H. N. Org. Syn. 1965, 45, 47.
25. Cama, L. D.; Leanza, W. J.; Beattie, T. R.; Christensen, B. G. J. Am. Chem. Soc. 1972, 94, 1408; Moore, A. T.; Rydon, H. N. Org. Syn. 1965, 45, 47.
26. 3) and concentrated to afford 245g of the crude azidoalcohol 3a (an oil, quant. yield). To the 245 g of crude product in 1.6L ethanol was added 10g of Pd/C, followed by slow addition of 170 ml (1.02mole) of 6N HCl solution. The resulting solution was stirred under hydrogen at room temperature and room pressure for 40h, followed by addition of 1.5L water and filtration through Celite. The filtrate was concentrated to remove most of the ethanol, then 200ml of 6N NaOH solution was added slowly to generate the free base which precipitated spontaneously. The resulting suspension was filtered, washed with 500mL water, and dried to afford 183g of the crude product. The first recrystallization from 400mL of anhydrous ethanol gave 158.5g (>99% ee). Recrystallization of the concentrated mother liquors from 50mL of ethanol afforded another 13.8g (>99% ee). These were combined to give 172.3g (>99% ee and 81% overall yield from the diol).
27. D - 28.8° (c=1.06, MeOH). ee determination: the N-tosyl 3-amino 1.2-propanediol derived from 4f was analyzed, HPLC: Chiralcel AD, 15% i-PrOH/Hexane, 0.5mL/min; 55.7, 39.5.