Convenient preparation of optically pure 1,3-diaryl-1,3-propanediols

Synlett

Volumn , Issue 4, 2000, Pages 535-537

  Ohtsuka, Yuhki ^a   Kubota, Takeshi ^a   Ikeno, Taketo ^a   Nagata, Takushi ^b   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

^b MITSUI CHEMICALS INC   (Japan)

Author keywords

Asymmetric synthesis; Borohydride; Cobalt; Diols; Reductions

Indexed keywords

COBALT; PROPANEDIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; OPTICAL ROTATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0034082849     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483; Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1998, 37, 2580.
2. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483; Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1998, 37, 2580.
3. For examples; Kawashima, M.; Hirayama, A. Chem. Lett. 1991, 763; Pikul, S.; Corey, E. J. Org. Synth. 1992, 71, 22.
4. For examples; Kawashima, M.; Hirayama, A. Chem. Lett. 1991, 763; Pikul, S.; Corey, E. J. Org. Synth. 1992, 71, 22.
5. Hydrogenation of the corresponding 1,3-diketones by homogeneous catalysts; Kitamura, M.; Ohkuma.T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629; Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc., Chem. Commun. 1988, 87; Pini, D; Mandoli, A.; Iuliano, A.; Salavadori, P. Tetrahedron:Asymmetry 1995, 6, 1031; Highly enantioselective and diastereoselective hydrogenation was recently reported. Ireland, T.; Grossheimann, G.; Wieser-Jeunessc, C.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 3212.
6. Hydrogenation of the corresponding 1,3-diketones by homogeneous catalysts; Kitamura, M.; Ohkuma.T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629; Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc., Chem. Commun. 1988, 87; Pini, D; Mandoli, A.; Iuliano, A.; Salavadori, P. Tetrahedron:Asymmetry 1995, 6, 1031; Highly enantioselective and diastereoselective hydrogenation was recently reported. Ireland, T.; Grossheimann, G.; Wieser-Jeunessc, C.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 3212.
7. Hydrogenation of the corresponding 1,3-diketones by homogeneous catalysts; Kitamura, M.; Ohkuma.T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629; Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc., Chem. Commun. 1988, 87; Pini, D; Mandoli, A.; Iuliano, A.; Salavadori, P. Tetrahedron:Asymmetry 1995, 6, 1031; Highly enantioselective and diastereoselective hydrogenation was recently reported. Ireland, T.; Grossheimann, G.; Wieser-Jeunessc, C.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 3212.
8. Hydrogenation of the corresponding 1,3-diketones by homogeneous catalysts; Kitamura, M.; Ohkuma.T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629; Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc., Chem. Commun. 1988, 87; Pini, D; Mandoli, A.; Iuliano, A.; Salavadori, P. Tetrahedron:Asymmetry 1995, 6, 1031; Highly enantioselective and diastereoselective hydrogenation was recently reported. Ireland, T.; Grossheimann, G.; Wieser-Jeunessc, C.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 3212.
9. Hydrogenation by heterogeneous catalysts; Ito, K.; Harada, T.; Tai, A. Bull. Chem. Soc. Jpn. 1980, 53, 3367.
10. Kinetic resolution by Sharpless epoxidation of allylic alcohols derived from chalcone; Roos, G. H. P.; Donovan, A. R. Synlett 1996, 1189; Roos, G. H. P.; Donovan, A. R. Tetrahedron:Asymmetry 1999, 10, 991.
11. Kinetic resolution by Sharpless epoxidation of allylic alcohols derived from chalcone; Roos, G. H. P.; Donovan, A. R. Synlett 1996, 1189; Roos, G. H. P.; Donovan, A. R. Tetrahedron:Asymmetry 1999, 10, 991.
12. Microbial resolution of the corresponding diacetates; Yamamoto, K.; Ando, H.; Chikamatsu, H. J. Chem. Soc., Chem. Commun. 1987, 334.
13. Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2145; Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1997, 493.
14. Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2145; Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1997, 493.
15. It was reported that the highly enantioselective reduction of ketones was achieved by using modified borohydride with tetrahydrofurfuryl alcohol and ethanol; Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1996, 737.
16. Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345.
17. 2O/pyridine to be 84/16.
18. It was reported that appropriate choice of the additive alcohols according to the substrates was important to achieve high enantiomeric excesses in the asymmetric reduction of ketones; Nagata, T.; Sugi, K. D.; Yamada, T.; Mukaiyama, T. Synlett 1996, 1076.
19. 2. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. Solvent and tetrahydrofurfuryl alcohol were removed under reduced pressure. The crude products were rinsed with ethyl acetate/ hexane and recrystallized from ethyl acetate to obtain the optically pure (15,35)-1,3-diphenyl-1,3-propanediol in 60% yield (6.15 g).
20. Optically pure 1,3-diaryl-1,3-propanediols were quantitatively converted to the corresponding 1,3-diamines without any loss of optical purity; see reference 5; Pini, D.; Iuliano, C.; Salavadori, P. Synthesis 1990, 1023.