메뉴 건너뛰기




Volumn 11, Issue 9, 2000, Pages 2037-2044

Asymmetric photodeconjugation of ammonium ene-carboxylates: Temperature effects and evidence for the α-carbon of the dienolic species as a latent trigonal centre

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE;

EID: 0038160645     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00151-8     Document Type: Article
Times cited : (33)

References (54)
  • 1
    • 0001084079 scopus 로고
    • Reviews: (a)
    • Reviews: (a) Duhamel, L; Duhamel, P.; Launay, J.-C.; Plaquevent, J.-C. Bull. Soc. Chim. Fr. 1984, II-421. (b) Fehr, C. Chimia 1991, 45, 253. (c) Hünig, S. In Stereoselective Synthesis (Houben-Weyl); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme Verlag: New York, 1996; p. 3811. (d) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566.
    • (1984) Bull. Soc. Chim. Fr.
    • Duhamel, L.1    Duhamel, P.2    Launay, J.-C.3    Plaquevent, J.-C.4
  • 2
    • 0001129994 scopus 로고
    • (b)
    • Reviews: (a) Duhamel, L; Duhamel, P.; Launay, J.-C.; Plaquevent, J.-C. Bull. Soc. Chim. Fr. 1984, II-421. (b) Fehr, C. Chimia 1991, 45, 253. (c) Hünig, S. In Stereoselective Synthesis (Houben-Weyl); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme Verlag: New York, 1996; p. 3811. (d) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566.
    • (1991) Chimia , vol.45 , pp. 253
    • Fehr, C.1
  • 3
    • 4243690204 scopus 로고    scopus 로고
    • (c) Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme Verlag: New York
    • Reviews: (a) Duhamel, L; Duhamel, P.; Launay, J.-C.; Plaquevent, J.-C. Bull. Soc. Chim. Fr. 1984, II-421. (b) Fehr, C. Chimia 1991, 45, 253. (c) Hünig, S. In Stereoselective Synthesis (Houben-Weyl); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme Verlag: New York, 1996; p. 3811. (d) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566.
    • (1996) In Stereoselective Synthesis (Houben-Weyl) , pp. 3811
    • Hünig, S.1
  • 4
    • 33751146774 scopus 로고    scopus 로고
    • (d)
    • Reviews: (a) Duhamel, L; Duhamel, P.; Launay, J.-C.; Plaquevent, J.-C. Bull. Soc. Chim. Fr. 1984, II-421. (b) Fehr, C. Chimia 1991, 45, 253. (c) Hünig, S. In Stereoselective Synthesis (Houben-Weyl); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme Verlag: New York, 1996; p. 3811. (d) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2566
    • Fehr, C.1
  • 10
    • 0343521066 scopus 로고    scopus 로고
    • 5 the highest priority to the hydroxylic function which gave the enolate or which is linked to the inductor during the selective step of protonation
    • 5 the highest priority to the hydroxylic function which gave the enolate or which is linked to the inductor during the selective step of protonation.
  • 11
    • 0002652021 scopus 로고
    • (a) Morrison, J. D., Ed.; Academic Press: Orlando
    • (a) Evans, D. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1984; Vol. 3, p. 11.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 11
    • Evans, D.A.1
  • 15
    • 0342650832 scopus 로고    scopus 로고
    • If E- and Z-enolates give rise to high but opposite induction, the enantiofacial selectivity will be determined entirely by the substituents at C-1 (C-α) of the enolate, the substituents at C-2 being non-discriminating (latent C-β). If the same facial selectivity is observed from Z- and E-enolates, the control will proceed from C-β substituents (latent C-α)
    • If E- and Z-enolates give rise to high but opposite induction, the enantiofacial selectivity will be determined entirely by the substituents at C-1 (C-α) of the enolate, the substituents at C-2 being non-discriminating (latent C-β). If the same facial selectivity is observed from Z- and E-enolates, the control will proceed from C-β substituents (latent C-α).
  • 16
    • 0030724513 scopus 로고    scopus 로고
    • For more recent examples than Ref. 1d, see: (a)
    • For more recent examples than Ref. 1d, see: (a) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (b) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (c) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. J. Chem. Soc., Chem. Commun. 1997, 1857. (c) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. (d) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (e) Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. (f) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2366
    • Sugiura, M.1    Nakai, T.2
  • 17
    • 0030773296 scopus 로고    scopus 로고
    • (b)
    • For more recent examples than Ref. 1d, see: (a) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (b) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (c) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. J. Chem. Soc., Chem. Commun. 1997, 1857. (c) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. (d) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (e) Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. (f) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 3293
    • Takahashi, T.1    Nakao, N.2    Koizumi, T.3
  • 18
    • 0002636545 scopus 로고    scopus 로고
    • (c)
    • For more recent examples than Ref. 1d, see: (a) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (b) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (c) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. J. Chem. Soc., Chem. Commun. 1997, 1857. (c) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. (d) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (e) Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. (f) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1997) J. Chem. Soc., Chem. Commun. , pp. 1857
    • Kosugi, H.1    Abe, M.2    Hatsudar3    Uda, H.4    Kato, M.5
  • 19
    • 0030839482 scopus 로고    scopus 로고
    • (c)
    • For more recent examples than Ref. 1d, see: (a) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (b) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (c) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. J. Chem. Soc., Chem. Commun. 1997, 1857. (c) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. (d) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (e) Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. (f) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6861
    • Kosugi, H.1    Hoshino, K.2    Uda, H.3
  • 20
    • 0030717149 scopus 로고    scopus 로고
    • (d)
    • For more recent examples than Ref. 1d, see: (a) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (b) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (c) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. J. Chem. Soc., Chem. Commun. 1997, 1857. (c) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. (d) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (e) Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. (f) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7759
    • Tsunoda, T.1    Kaku, H.2    Nagaku, M.3    Okuyama, E.4
  • 21
    • 0001961783 scopus 로고    scopus 로고
    • (e)
    • For more recent examples than Ref. 1d, see: (a) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (b) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (c) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. J. Chem. Soc., Chem. Commun. 1997, 1857. (c) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. (d) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (e) Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. (f) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1998) J. Chem. Soc., Chem. Commun. , pp. 1573
    • Yanagisawa, A.1    Inanami, H.2    Yamamoto, H.3
  • 22
    • 0033553373 scopus 로고    scopus 로고
    • (f)
    • For more recent examples than Ref. 1d, see: (a) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (b) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293. (c) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. J. Chem. Soc., Chem. Commun. 1997, 1857. (c) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. (d) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (e) Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. (f) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3939
    • Asensio, G.1    Cuenca, A.2    Gavina, P.3    Medio-Simon, M.4
  • 34
    • 0342650829 scopus 로고    scopus 로고
    • (c) See also Ref. 1d
    • (c) See also Ref. 1d.
  • 36
    • 0343085027 scopus 로고    scopus 로고
    • (a) Review
    • (a) Review: Itoh, Y. Synthesis 1998, 1.
    • (1998) Synthesis , pp. 1
    • Itoh, Y.1
  • 40
    • 0343085026 scopus 로고
    • This non-racemizing procedure is commonly applied in peptide synthesis Wiley: New York
    • This non-racemizing procedure is commonly applied in peptide synthesis: Fieser, M. Reagents for Organic Synthesis; Wiley: New York, 1986; Vol. 12, p. 199.
    • (1986) Reagents for Organic Synthesis , vol.12 , pp. 199
    • Fieser, M.1
  • 42
    • 0343521060 scopus 로고    scopus 로고
    • 21
    • 21.
  • 47
    • 0343085024 scopus 로고    scopus 로고
    • 22
    • 22.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.