Efficient synthesis of enantiopure 1,2-bis(hydroxymethyl)-3,3-difluorocyclopropane derivatives through lipase-catalyzed reaction

Chemistry Letters

Volumn , Issue 9, 1998, Pages 903-904

  Itoh, Toshiyuki ^a   Mitsukura, Koichi ^a   Furutani, Miyuki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032353048     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.903     Document Type: Article

References (15)

1. Preliminary results of this project have been reported: T. Itoh, "Research Results for Scientific Research on Priority Areas (No. 283, "Innovative Synthetic Reactions") from The Ministry of Education, Science, Sports and Culture of Japan," pp11-12 (1998).; K. Mitsukura and T. Itoh, 47th Annual Meeting of Chemical Society of Japan, 3D537 (Kyoto, 1998).
2. Preliminary results of this project have been reported: T. Itoh, "Research Results for Scientific Research on Priority Areas (No. 283, "Innovative Synthetic Reactions") from The Ministry of Education, Science, Sports and Culture of Japan," pp11-12 (1998).; K. Mitsukura and T. Itoh, 47th Annual Meeting of Chemical Society of Japan, 3D537 (Kyoto, 1998).
3. M. H. Gelb, J. P. Svaren, and R. H. Abeles, Biochemistry, 24, 1813 (1985). For a recent review of this field see: M. J. Tozer and T. F. Herpin, Tetrahedron, 52, 8619 (1996).
4. M. H. Gelb, J. P. Svaren, and R. H. Abeles, Biochemistry, 24, 1813 (1985). For a recent review of this field see: M. J. Tozer and T. F. Herpin, Tetrahedron, 52, 8619 (1996).
5. For recent examples see. a) A. G. M. Barrett and W. Tam. J. Org. Chem., 62, 7673 (1997).
6. b) A. G. M. Barrett and W. Tam. J. Org. Chem., 62, 4653 (1997) and references cited therein.
7. For reviews see. a) J. T. Welch, Tetrahedron, 43, 3123 (1987).
8. b) G. Resnati, Tetrahedron, 49, 9385 (1993).
9. Some cytotoxic activity for an uracil analogue of 1, i.e. (±)-(2,2-difluoro-3-hydroxymethyl-cyclopropylmethyl)uracil has been reported: R. Csuk, and L. Eversmann, Tetrahedron, 54, 6445 (1998).
10. The enzymatic method is very useful for synthesizing fluorinated organic compounds. For a good review in this field see: T. Kitazume and T. Yamazaki, "Topics in Current Chemistry," Springer Verlag (1997), Vol. 193, pp91-130.
11. For our review in this field see: T. Itoh, Y. Takagi, and H. Tsukube, J. Molecular Catalysis B: Enzymatic, 3, 261 (1997).
12. T. Taguchi, M. Kurishita, A. Shibuya, and K. Aso, Tetrahedron, 53, 9497 (1997).
13. a) P. Crabbé, H. Carpio, E. Velarde, and J. H. Fried. J. Org. Chem., 38, 1478 (1973).
14. b) D. L. S. Brahms and W. P. Dailey, Chem. Rev., 96, 1585 (1996).
15. The absolute configuration of 1 produced was a tentative one.