Efficient kinetic resolution of (±)-4-methyl-Hajos-Parrish ketone by baker's yeast reduction

Tetrahedron Asymmetry

Volumn 11, Issue 3, 2000, Pages 829-834

  Hioki, Hideaki ^a   Hashimoto, Takefumi ^a   Kodama, Mitsuaki ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; ENANTIOMER; PRIORITY JOURNAL; REDUCTION; YEAST;

EID: 0034712278     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00010-0     Document Type: Article

References (19)

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3. For preparation of (+)-2b using amino acid catalyzed aldol reaction, see: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497. (b) Banerjee, D. K.; Kasturi, T. R.; Sarkar, A. Proc. Ind. Acad. Sci., Chem. Sci. 1983, 92, 181-187. (c) Paquette, L. A.; Wang, T.-Z.; Sivik, M. R. J. Am. Chem. Soc. 1994, 116, 11323-11334. (d) Ohtsuka, M.; Takekawa, Y.; Shishido, K. Tetrahedron Lett. 1998, 39, 5803-5806. (e) Sakai, H; Hagiwara, H.; Ito, Y.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1999, 40, 2965-2968.
4. For preparation of (+)-2b using amino acid catalyzed aldol reaction, see: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497. (b) Banerjee, D. K.; Kasturi, T. R.; Sarkar, A. Proc. Ind. Acad. Sci., Chem. Sci. 1983, 92, 181-187. (c) Paquette, L. A.; Wang, T.-Z.; Sivik, M. R. J. Am. Chem. Soc. 1994, 116, 11323-11334. (d) Ohtsuka, M.; Takekawa, Y.; Shishido, K. Tetrahedron Lett. 1998, 39, 5803-5806. (e) Sakai, H; Hagiwara, H.; Ito, Y.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1999, 40, 2965-2968.
5. For preparation of (+)-2b using amino acid catalyzed aldol reaction, see: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497. (b) Banerjee, D. K.; Kasturi, T. R.; Sarkar, A. Proc. Ind. Acad. Sci., Chem. Sci. 1983, 92, 181-187. (c) Paquette, L. A.; Wang, T.-Z.; Sivik, M. R. J. Am. Chem. Soc. 1994, 116, 11323-11334. (d) Ohtsuka, M.; Takekawa, Y.; Shishido, K. Tetrahedron Lett. 1998, 39, 5803-5806. (e) Sakai, H; Hagiwara, H.; Ito, Y.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1999, 40, 2965-2968.
6. For preparation of (+)-2b using amino acid catalyzed aldol reaction, see: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497. (b) Banerjee, D. K.; Kasturi, T. R.; Sarkar, A. Proc. Ind. Acad. Sci., Chem. Sci. 1983, 92, 181-187. (c) Paquette, L. A.; Wang, T.-Z.; Sivik, M. R. J. Am. Chem. Soc. 1994, 116, 11323-11334. (d) Ohtsuka, M.; Takekawa, Y.; Shishido, K. Tetrahedron Lett. 1998, 39, 5803-5806. (e) Sakai, H; Hagiwara, H.; Ito, Y.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1999, 40, 2965-2968.
7. For preparation of (+)-2b using amino acid catalyzed aldol reaction, see: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497. (b) Banerjee, D. K.; Kasturi, T. R.; Sarkar, A. Proc. Ind. Acad. Sci., Chem. Sci. 1983, 92, 181-187. (c) Paquette, L. A.; Wang, T.-Z.; Sivik, M. R. J. Am. Chem. Soc. 1994, 116, 11323-11334. (d) Ohtsuka, M.; Takekawa, Y.; Shishido, K. Tetrahedron Lett. 1998, 39, 5803-5806. (e) Sakai, H; Hagiwara, H.; Ito, Y.; Hoshi, T.; Suzuki, T.; Ando, M. Tetrahedron Lett. 1999, 40, 2965-2968.
8. For examples of kinetic resolution of bicyclic ketones by baker's yeast, see: (a) Hoffmann, G.; Wiartalla, R. Tetrahedron Lett. 1982, 23, 3887-2968. (b) Inaymna, S.; Shimizu, N.; Ohkura, T.; Akita, H.; Ohishi, T.; Iitaka, Y. Chem. Pharm. Bull. 1986, 34, 2660-2663.
9. For examples of kinetic resolution of bicyclic ketones by baker's yeast, see: (a) Hoffmann, G.; Wiartalla, R. Tetrahedron Lett. 1982, 23, 3887-2968. (b) Inaymna, S.; Shimizu, N.; Ohkura, T.; Akita, H.; Ohishi, T.; Iitaka, Y. Chem. Pharm. Bull. 1986, 34, 2660-2663.
10. For examples of baker's yeast reduction of 2,2′-disubstituted 1,3-cyclopentadiones, see: (a) Komsol, H.; Kieslich, R.; Vössing, H.; Koch, H.-J.; Petzoldt, K.; Gibian, H. Liebigs Ann. Chem. 1967, 701, 199-205. (b) Lanzilotta, R. P.; Bradley, D. P.; Beard, C. C. Appl. Microbiology 1975, 29, 427-429.
11. For examples of baker's yeast reduction of 2,2′-disubstituted 1,3-cyclopentadiones, see: (a) Komsol, H.; Kieslich, R.; Vössing, H.; Koch, H.-J.; Petzoldt, K.; Gibian, H. Liebigs Ann. Chem. 1967, 701, 199-205. (b) Lanzilotta, R. P.; Bradley, D. P.; Beard, C. C. Appl. Microbiology 1975, 29, 427-429.
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16. (a) Stereochemistry of (-)-5 was determined by the comparison with their reported sign of specific rotation. Buchschacher, P.; Fürst, A.; Gutzwiller, J. Org. Synth. Coll. Vol. VII 1990, 368-372.
17. 4 reduction of (-)-5; see: Yeo, S.-K.; Hatae, N.; Kanematsu, K. Tetrahedron 1995, 51, 3499-3506.
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19. Ramachandran, S.; Newman, M. Org. Synth. Coll. Vol. V 1973, 486-489.