Enzyme-catalyzed asymmetrization of 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl esters

Tetrahedron Letters

Volumn 38, Issue 24, 1997, Pages 4243-4246

  Akai, Shuji ^a   Naka, Tadaatsu ^a   Takebe, Yasushi ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; ENZYME ACTIVITY; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030972841     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00855-1     Document Type: Article

References (22)

1. Fuji, K. Chem. Rev. 1993, 93, 2037-2066.
2. Just before completion of this paper, the first example of the asymmetrization of prochiral 2,2-disubstituted 1,3-propanediols was reported using isopropenyl acetate. See, Fadel, A.; Arzel, P. Tetrahedron: Asym. 1997, 8, 283-291.
3. 1 The process of Scheme 1 is advantageous because it can be run in organic solvents.
4. Recent examples, see; a) Fadel, A.; Garcia-Argote, S. Tetrahedron: Asym. 1996, 7, 1159-1166 and references cited therein;
5. b) Hallinan, K. O.; Honda, T. Tetrahedron 1995, 57, 12211-12216.
6. Suemune, H.; Harabe, T.; Xie, Z.-F.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 4337-4344; For the related hydrolysis of 2,2-disubstituted 1,3-propanediyl diesters, see, Prasad, K.; Estermann, H.; Chen, C.-P.; Repic, O.; Hardtmann, G. E. Tetrahedron: Asym. 1990, 1, 421-424; Seu, Y.-B.; Kho, Y.-H. Tetrahedron Lett. 1992, 33, 7015-7016; Ito, T.; Ohara, H.; Takagi, Y.; Kanda, N.; Uneyama, K. ibid. 1993, 34, 4215-4218.
7. Suemune, H.; Harabe, T.; Xie, Z.-F.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 4337-4344; For the related hydrolysis of 2,2-disubstituted 1,3-propanediyl diesters, see, Prasad, K.; Estermann, H.; Chen, C.-P.; Repic, O.; Hardtmann, G. E. Tetrahedron: Asym. 1990, 1, 421-424; Seu, Y.-B.; Kho, Y.-H. Tetrahedron Lett. 1992, 33, 7015-7016; Ito, T.; Ohara, H.; Takagi, Y.; Kanda, N.; Uneyama, K. ibid. 1993, 34, 4215-4218.
8. Suemune, H.; Harabe, T.; Xie, Z.-F.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 4337-4344; For the related hydrolysis of 2,2-disubstituted 1,3-propanediyl diesters, see, Prasad, K.; Estermann, H.; Chen, C.-P.; Repic, O.; Hardtmann, G. E. Tetrahedron: Asym. 1990, 1, 421-424; Seu, Y.-B.; Kho, Y.-H. Tetrahedron Lett. 1992, 33, 7015-7016; Ito, T.; Ohara, H.; Takagi, Y.; Kanda, N.; Uneyama, K. ibid. 1993, 34, 4215-4218.
9. Suemune, H.; Harabe, T.; Xie, Z.-F.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 4337-4344; For the related hydrolysis of 2,2-disubstituted 1,3-propanediyl diesters, see, Prasad, K.; Estermann, H.; Chen, C.-P.; Repic, O.; Hardtmann, G. E. Tetrahedron: Asym. 1990, 1, 421-424; Seu, Y.-B.; Kho, Y.-H. Tetrahedron Lett. 1992, 33, 7015-7016; Ito, T.; Ohara, H.; Takagi, Y.; Kanda, N.; Uneyama, K. ibid. 1993, 34, 4215-4218.
10. Reviews: Faber, K.; Riva, S. Synthesis 1992, 895-910; Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140; Theil, F. ibid. 1995, 95, 2203-2227; Nakamura, K.; Hirose, Y. J. Synth. Org. Chem., Jpn. 1995, 53, 668-677.
11. Reviews: Faber, K.; Riva, S. Synthesis 1992, 895-910; Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140; Theil, F. ibid. 1995, 95, 2203-2227; Nakamura, K.; Hirose, Y. J. Synth. Org. Chem., Jpn. 1995, 53, 668-677.
12. Reviews: Faber, K.; Riva, S. Synthesis 1992, 895-910; Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140; Theil, F. ibid. 1995, 95, 2203-2227; Nakamura, K.; Hirose, Y. J. Synth. Org. Chem., Jpn. 1995, 53, 668-677.
13. Reviews: Faber, K.; Riva, S. Synthesis 1992, 895-910; Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140; Theil, F. ibid. 1995, 95, 2203-2227; Nakamura, K.; Hirose, Y. J. Synth. Org. Chem., Jpn. 1995, 53, 668-677.
14. Kita, Y.; Takebe, Y.; Murata, K.; Naka, T.; Akai, S. Tetrahedron Lett. 1996, 37, 7369-7372.
15. A very similar concept using 1-ethoxyvinyl acetate for the enzymatic resolution of alcohols was also very recently reported. See, Schudok, M.; Kretzschmar, G. Tetrahedron Lett. 1997, 38, 387-388.
16. Kita, Y.; Maeda, H.; Omori, K.; Okuno, T.; Tamura, Y. J. Chem. Soc., Perkin Trans. 1 1993, 2999-3005; Shibata, N.; Matsugi, M.; Kawano, N.; Fukui, S.; Fujimori, C.; Gotanda, K.; Murata, K.; Kita, Y. Tetrahedron: Asym. 1997, 8, 303-310.
17. Kita, Y.; Maeda, H.; Omori, K.; Okuno, T.; Tamura, Y. J. Chem. Soc., Perkin Trans. 1 1993, 2999-3005; Shibata, N.; Matsugi, M.; Kawano, N.; Fukui, S.; Fujimori, C.; Gotanda, K.; Murata, K.; Kita, Y. Tetrahedron: Asym. 1997, 8, 303-310.
18. 4a Based on the similarity of the specific rotation of 7f to that of 3f, its absolute stereochemistry was speculated to be S. (formula presented)
19. For the use of resolution of a racemic alcohol, see; Tamazaki, Y.; Hosono, K. Tetrahedron Lett. 1990, 31, 3895-3896. Other examples are on the use for the site selective acylation of sugars. See, Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221; Panza, L.; Brasca, S.; Riva, S.; Russo, G. Tetrahedron: Asym. 1993, 4, 931-932.
20. For the use of resolution of a racemic alcohol, see; Tamazaki, Y.; Hosono, K. Tetrahedron Lett. 1990, 31, 3895-3896. Other examples are on the use for the site selective acylation of sugars. See, Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221; Panza, L.; Brasca, S.; Riva, S.; Russo, G. Tetrahedron: Asym. 1993, 4, 931-932.
21. For the use of resolution of a racemic alcohol, see; Tamazaki, Y.; Hosono, K. Tetrahedron Lett. 1990, 31, 3895-3896. Other examples are on the use for the site selective acylation of sugars. See, Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221; Panza, L.; Brasca, S.; Riva, S.; Russo, G. Tetrahedron: Asym. 1993, 4, 931-932.
22. Under basic conditions (pyridine/room temperature/1 d, imidazole/DMF/room temperature/1 d), 3a and 3f did not change at all.