Lipase-triethylamine-mediated dynamic transesterification of a tricyclic acyloin having a latent meso-structure: A new route to optically pure oxodicyclopentadiene

Chemical Communications

Volumn , Issue 15, 1997, Pages 1399-1400

  Taniguchi, Takahiko ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002882091     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702910a     Document Type: Article

References (17)

1. R. D. Miller, D. L. Dolce and V. Y. Merritt, J. Org. Chem., 1976, 41, 1221.
2. cf. T. Taniguchi, Y. Goto and K. Ogasawara, Synlett, in the press.
3. (a) K. Tanaka and K. Ogasawara, Synthesis, 1995, 1237;
4. (b) T. Sugahara, Y. Kuroyanagi and K. Ogasawara, Synthesis, 1996, 1101.
5. For reviews on dynamic kinetic resolution, see R. S. Ward, Tetrahedron: Asymmetry, 1995, 6, 1475; H. Stecher and K. Faber, Synthesis, 1997, 1.
6. For reviews on dynamic kinetic resolution, see R. S. Ward, Tetrahedron: Asymmetry, 1995, 6, 1475; H. Stecher and K. Faber, Synthesis, 1997, 1.
7. For recent examples, see (a) N. J. Turner, J. R. Winterman, R. NcCague, J. S. Paratt and J. C. Taylor, Tetrahedron Lett., 1995, 36, 1113; (b) J. V. Allen and J. M. J. Williams, Tetrahedron Lett., 1996, 37, 1859; (c) M. van den Heuvel, A. D. Cuiper, H. van der Deen, R. M. Kellogg and B. L. Feringa, Tetrahedron Lett., 1997, 38, 1655. For a non-dynamic kinetic resolution of acyloins, see D. Gala, D. J. DiBenedetto, J. E. Clark, B. L. Murphy, D. P. Schumacher and M. Steinman, Tetrahedron Lett., 1996, 37, 611; W. Adam, M. T. Maria, R. T. Fell and C. R. Saha-Moeller, Tetrahedron: Asymmetry, 1996, 7, 2207.
8. For recent examples, see (a) N. J. Turner, J. R. Winterman, R. NcCague, J. S. Paratt and J. C. Taylor, Tetrahedron Lett., 1995, 36, 1113; (b) J. V. Allen and J. M. J. Williams, Tetrahedron Lett., 1996, 37, 1859; (c) M. van den Heuvel, A. D. Cuiper, H. van der Deen, R. M. Kellogg and B. L. Feringa, Tetrahedron Lett., 1997, 38, 1655. For a non-dynamic kinetic resolution of acyloins, see D. Gala, D. J. DiBenedetto, J. E. Clark, B. L. Murphy, D. P. Schumacher and M. Steinman, Tetrahedron Lett., 1996, 37, 611; W. Adam, M. T. Maria, R. T. Fell and C. R. Saha-Moeller, Tetrahedron: Asymmetry, 1996, 7, 2207.
9. For recent examples, see (a) N. J. Turner, J. R. Winterman, R. NcCague, J. S. Paratt and J. C. Taylor, Tetrahedron Lett., 1995, 36, 1113; (b) J. V. Allen and J. M. J. Williams, Tetrahedron Lett., 1996, 37, 1859; (c) M. van den Heuvel, A. D. Cuiper, H. van der Deen, R. M. Kellogg and B. L. Feringa, Tetrahedron Lett., 1997, 38, 1655. For a non-dynamic kinetic resolution of acyloins, see D. Gala, D. J. DiBenedetto, J. E. Clark, B. L. Murphy, D. P. Schumacher and M. Steinman, Tetrahedron Lett., 1996, 37, 611; W. Adam, M. T. Maria, R. T. Fell and C. R. Saha-Moeller, Tetrahedron: Asymmetry, 1996, 7, 2207.
10. For recent examples, see (a) N. J. Turner, J. R. Winterman, R. NcCague, J. S. Paratt and J. C. Taylor, Tetrahedron Lett., 1995, 36, 1113; (b) J. V. Allen and J. M. J. Williams, Tetrahedron Lett., 1996, 37, 1859; (c) M. van den Heuvel, A. D. Cuiper, H. van der Deen, R. M. Kellogg and B. L. Feringa, Tetrahedron Lett., 1997, 38, 1655. For a non-dynamic kinetic resolution of acyloins, see D. Gala, D. J. DiBenedetto, J. E. Clark, B. L. Murphy, D. P. Schumacher and M. Steinman, Tetrahedron Lett., 1996, 37, 611; W. Adam, M. T. Maria, R. T. Fell and C. R. Saha-Moeller, Tetrahedron: Asymmetry, 1996, 7, 2207.
11. For recent examples, see (a) N. J. Turner, J. R. Winterman, R. NcCague, J. S. Paratt and J. C. Taylor, Tetrahedron Lett., 1995, 36, 1113; (b) J. V. Allen and J. M. J. Williams, Tetrahedron Lett., 1996, 37, 1859; (c) M. van den Heuvel, A. D. Cuiper, H. van der Deen, R. M. Kellogg and B. L. Feringa, Tetrahedron Lett., 1997, 38, 1655. For a non-dynamic kinetic resolution of acyloins, see D. Gala, D. J. DiBenedetto, J. E. Clark, B. L. Murphy, D. P. Schumacher and M. Steinman, Tetrahedron Lett., 1996, 37, 611; W. Adam, M. T. Maria, R. T. Fell and C. R. Saha-Moeller, Tetrahedron: Asymmetry, 1996, 7, 2207.
12. cf. F. Theil, S. Ballschuh, A. Kunath and H. Schick, Tetrahedron: Asymmetry, 1991, 2, 1031; F. Theil, J. Weidner, S. Ballschuh, A. Kunath and H. Schick, Tetrahedron Lett., 1993, 34, 305; T. Sugahara and K. Ogasawara, Tetrahedron Lett., 1996, 37, 205.
13. cf. F. Theil, S. Ballschuh, A. Kunath and H. Schick, Tetrahedron: Asymmetry, 1991, 2, 1031; F. Theil, J. Weidner, S. Ballschuh, A. Kunath and H. Schick, Tetrahedron Lett., 1993, 34, 305; T. Sugahara and K. Ogasawara, Tetrahedron Lett., 1996, 37, 205.
14. cf. F. Theil, S. Ballschuh, A. Kunath and H. Schick, Tetrahedron: Asymmetry, 1991, 2, 1031; F. Theil, J. Weidner, S. Ballschuh, A. Kunath and H. Schick, Tetrahedron Lett., 1993, 34, 305; T. Sugahara and K. Ogasawara, Tetrahedron Lett., 1996, 37, 205.
15. S. Takano, K. Inomata and K. Ogasawara, Chem. Lett., 1989, 359.
16. For a pertinent review, see K. Ogasawara, J. Synth. Org. Chem. Jpn., 1996, 54, 15.
17. For a recent synthesis of optically active 8, see J. Knol and B. L. Feringa, Tetrahedron Lett., 1997, 38, 2527 and references cited therein.