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Volumn 109, Issue 19, 1987, Pages 5765-5780

Catalytic Asymmetric Epoxidation and Kinetic Resolution: Modified Procedures Including in Situ Derivatization

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EID: 18844410382     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00253a032     Document Type: Article
Times cited : (2211)

References (37)
  • 2
    • 0001262297 scopus 로고
    • In Asymmetric Synthesis
    • Morrison, J. D., Ed.; Academic Press: New York, Chapter 8, 247. Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 7, 193. Pfenninger, A. Synthesis 1986, 89–116. The last of these reviews (Pfenninger) is somewhat out of date even for the stoichiometric reaction, especially with respect to the best experimental procedures and catalyst structure; the Asymmetric Synthesis reviews are more current.
    • Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 8, 247. Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 7, 193. Pfenninger, A. Synthesis 1986, 89–116. The last of these reviews (Pfenninger) is somewhat out of date even for the stoichiometric reaction, especially with respect to the best experimental procedures and catalyst structure; the Asymmetric Synthesis reviews are more current.
    • (1985) , vol.5
    • Finn, M.G.1    Sharpless, K.B.2
  • 3
    • 0042303174 scopus 로고
    • Dissertation
    • Massachusetts Institute of Technology, Cambridge, MA, Ph.D.
    • Finn, M. G. Ph.D. Dissertation, Massachusetts Institute of Technology, Cambridge, MA, 1985.
    • (1985)
    • Finn, M.G.1
  • 4
    • 85022975644 scopus 로고
    • Dissertation
    • Woodard, S. S. Ph.D. Dissertation, Stanford University, Stanford, CA, 1981.
    • (1981)
    • Woodard, S.S.1
  • 13
    • 0021721698 scopus 로고
    • (b) Masamune, H.; Sharpless, K. B., unpublished results. (19) Tuddenham, D.; Sharpless, K. B., unpublished results.
    • Bessodes, M.; Abushanab, E.; Antonakis, K. Tetrahedron Lett. 1984, 25, 5899. (b) Masamune, H.; Sharpless, K. B., unpublished results. (19) Tuddenham, D.; Sharpless, K. B., unpublished results.
    • (1984) Tetrahedron Lett. , vol.5899 , pp. 25
    • Bessodes, M.1    Abushanab, E.2    Antonakis, K.3
  • 14
    • 85022571875 scopus 로고    scopus 로고
    • In one instance, distillation of prenyl epoxy alcohol led to violent polymerization.
    • In situ derivatization avoids this problem.
    • In one instance, distillation of prenyl epoxy alcohol led to violent polymerization. In situ derivatization avoids this problem.
  • 16
    • 0020458548 scopus 로고
    • For uses of glycidol, see: Nakano, J.; Mimura, M.; Hayashida, M.; Kimura, K.; Nakanishi, T. Heterocycles 1983, 20, 1975. Haouet, A.; Sepulchre, M.; Spassky, N. Eur, Polym. J. 1983, 19, 1089. (b) For uses of crotyl epoxy alcohol, see: Kobayashi, Y.; Kitano, Y.; Sato, F. J. Chem. Soc.,Chem. Commun. 1984, 1329. Yamada, S.; Shiraishi, M.; Ohm-uri, M.; Takayama, H. Tetrahedron Lett. 1984, 25, 3347. Corey, E. J.; Trybulski, E. J.; Melvin, L. S.; Nicolaou, K. C.; Secrist, J. A.; Lett, R.; Sheldrake, P. W.; Falck, J. R.; Brunelle, D. J.; Haslanger, M. F.; Kim, S.; Yoo, S. J. Am. Chem. Soc. 1978,100, 4618. Helbig, W. Liebigs Ann. Chem. 1984, 1165. Kuroda, C.; Theramongkol, P.; Engebrecht, J. R.; White, J. D. J. Org. Chem. 1985, 51, 956. (c) For uses of prenyl epoxy alcohol, see: Dumont, R.; Pfander, H. Helv. Chim. Acta 1983, 66, 814. (22) For uses of glycidol derivatives, see: Hardy, J. C.; Villatte, G.; Gueremy, C. Bull. Soc. Chim. Fr. (Pt. 2) 1982, 304. McClure, D. E.; Arison, B. H.; Baldwin, J. J. J. Am. Chem. Soc. 1979, 101, 3666. Bouzoubaa, M.; Leclerc, G.; Rakhit, S.; Andermann, G. J. Med. Chem. 1985, 28, 896.
    • For uses of glycidol, see: Baldwin, J. J.; McClure, D. E.; Gross, D. M.; Williams, M. J. Med. Chem. 1982, 25, 931. Nakano, J.; Mimura, M.; Hayashida, M.; Kimura, K.; Nakanishi, T. Heterocycles 1983, 20, 1975. Haouet, A.; Sepulchre, M.; Spassky, N. Eur, Polym. J. 1983, 19, 1089. (b) For uses of crotyl epoxy alcohol, see: Kobayashi, Y.; Kitano, Y.; Sato, F. J. Chem. Soc.,Chem. Commun. 1984, 1329. Yamada, S.; Shiraishi, M.; Ohm-uri, M.; Takayama, H. Tetrahedron Lett. 1984, 25, 3347. Corey, E. J.; Trybulski, E. J.; Melvin, L. S.; Nicolaou, K. C.; Secrist, J. A.; Lett, R.; Sheldrake, P. W.; Falck, J. R.; Brunelle, D. J.; Haslanger, M. F.; Kim, S.; Yoo, S. J. Am. Chem. Soc. 1978,100, 4618. Helbig, W. Liebigs Ann. Chem. 1984, 1165. Kuroda, C.; Theramongkol, P.; Engebrecht, J. R.; White, J. D. J. Org. Chem. 1985, 51, 956. (c) For uses of prenyl epoxy alcohol, see: Dumont, R.; Pfander, H. Helv. Chim. Acta 1983, 66, 814. (22) For uses of glycidol derivatives, see: Hardy, J. C.; Villatte, G.; Gueremy, C. Bull. Soc. Chim. Fr. (Pt. 2) 1982, 304. McClure, D. E.; Arison, B. H.; Baldwin, J. J. J. Am. Chem. Soc. 1979, 101, 3666. Bouzoubaa, M.; Leclerc, G.; Rakhit, S.; Andermann, G. J. Med. Chem. 1985, 28, 896.
    • (1982) J. Med. Chem. , vol.25 , pp. 931
    • Baldwin, J.J.1    McClure, D.E.2    Gross, D.M.3    Williams, M.4
  • 17
    • 0001646756 scopus 로고
    • (b) Klunder, J. M.; Sharpless, K. B., unpublished results.
    • Klunder, J. M.; Sharpless, K. B. J. Org. Chem. 1987, 52, 2598. (b) Klunder, J. M.; Sharpless, K. B., unpublished results.
    • (1987) J. Org. Chem. , vol.52 , pp. 2598
    • Klunder, J.M.1    Sharpless, K.B.2
  • 19
    • 0021256675 scopus 로고
    • Williams, David R. (Indiana University), private communication.
    • Yamada, S.; Shiraishi, M.; Ohmori, M.; Takayama, H. Tetrahedron Lett. 1984, 25, 3347. Williams, David R. (Indiana University), private communication.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 3347
    • Yamada, S.1    Shiraishi, M.2    Ohmori, M.3    Takayama, H.4
  • 20
    • 0001017526 scopus 로고
    • The kinetic resolution of 2-methylenecyclohexanol is effective using 15 mol % catalyst in the presence of molecular sieves (R C. Ronald, private communication).
    • Roush, W. R.; Brown, R. J. J. Org. Chem. 1983, 48, 5093. The kinetic resolution of 2-methylenecyclohexanol is effective using 15 mol % catalyst in the presence of molecular sieves (R C. Ronald, private communication).
    • (1983) J. Org. Chem. , vol.48 , pp. 5093
    • Roush, W.R.1    Brown, R.J.2
  • 24
    • 85022526300 scopus 로고
    • Sumitomo Patent, Jpn. Kokai Tokkyo Koho JP 82 58 632
    • Sumitomo Patent, Jpn. Kokai Tokkyo Koho JP 82 58 632 (Chemical Abstracts 1982, 97, 144388 h).
    • (1982) Chemical Abstracts , vol.97 , pp. 144388
  • 25
    • 0000471716 scopus 로고
    • Prolonged heating beyond this time should be avoided since gradual TBHP decomposition occurs. However, interruption of the required heating period is acceptable
    • Prolonged heating beyond this time should be avoided since gradual TBHP decomposition occurs. However, interruption of the required heating period is acceptable, (b) Hill, J. G.; Rossiter, B. E.; Sharpless, K. B. J. Org. Chem. 1983, 48, 3607.
    • (1983) J. Org. Chem. , vol.48 , pp. 3607
    • Hill, J.G.1    Rossiter, B.E.2    Sharpless, K.B.3
  • 26
    • 0001034015 scopus 로고
    • Jones, T. K.; Denmark,S. E. Org. Synth. 1986, 64, 182.
    • Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595. Jones, T. K.; Denmark,S. E. Org. Synth. 1986, 64, 182.
    • (1982) J. Org. Chem. , vol.47 , pp. 4595
    • Denmark, S.E.1    Jones, T.K.2
  • 29
    • 0010640653 scopus 로고
    • (b) 7?.-(+)-a-Methoxy-a-(trifluoromethyl)phenylacetyl chloride
    • Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543. (b) 7?.-(+)-a-Methoxy-a-(trifluoromethyl)phenylacetyl chloride
    • (1969) J. Org. Chem. , vol.34 , pp. 2543
    • Dale, J.A.1    Dull, D.L.2    Mosher, H.S.3
  • 36
    • 84918708369 scopus 로고
    • This compound has previously been reported as the racemate. (b) Chautemps, P.; Pierre, j.L.; Arnaud, P. C. R. Seances Acad. Sci., Ser. 3 1968. 266, 622. This publication also describes the preparation of racemic epoxy crotyl tosylate. (c) Nakabayashi, N.; Masuhara, E.; Iwakara, Y. Bull. Chem. Soc. Jpn. 1966, 39, 413. (d) Ichikawa, K. Yuki Gosei Kagaku Kyokaishi 1964, 22, 553.
    • This compound has previously been reported as the racemate. (a) Pierre, J. L. ; Arnaud, P. Bull. Soc. Chim. Fr. 1969, 2868. (b) Chautemps, P.; Pierre, j.L.; Arnaud, P. C. R. Seances Acad. Sci., Ser. 3 1968. 266, 622. This publication also describes the preparation of racemic epoxy crotyl tosylate. (c) Nakabayashi, N.; Masuhara, E.; Iwakara, Y. Bull. Chem. Soc. Jpn. 1966, 39, 413. (d) Ichikawa, K. Yuki Gosei Kagaku Kyokaishi 1964, 22, 553.
    • (1969) Bull. Soc. Chim. Fr. , pp. 2868
    • Pierre, J.L.1    Arnaud, P.2


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