메뉴 건너뛰기




Volumn 122, Issue 19, 2000, Pages 4602-4607

Enantioselective enolate protonation with chiral anilines: Scope, structural requirements, and mechanistic implications

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE;

EID: 0034679019     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994437m     Document Type: Article
Times cited : (52)

References (60)
  • 5
    • 0001307549 scopus 로고    scopus 로고
    • (a) Reviews: Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2567. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2567
    • Fehr, C.1
  • 7
    • 0033538074 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio- Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1999) Tetrahedron , vol.55 , pp. 4595
    • Nakamura, Y.1    Takeuchi, S.2    Ohgo, Y.3    Yamaoka, M.4    Yoshida, A.5    Mikami, K.6
  • 8
    • 0033553373 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3939
    • Asensio, G.1    Cuenca, A.2    Gavina, P.3    Medio-Simon, M.4
  • 9
    • 0032573446 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio- Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 4073
    • Asensio, G.1    Aleman, P.2    Cuenca, A.3    Gil, J.4    Medio-Simon, M.5
  • 10
    • 0032547976 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio- Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8691
    • Takeuchi, S.1    Nakamura, Y.2    Ohgo, Y.3    Curran, D.P.4
  • 11
    • 0032509250 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio- Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1998) J. Org. Chem. , vol.63 , pp. 9342
    • Asensio, G.1    Aleman, P.2    Gil, J.3    Domingo, L.R.4    Medio-Simon, M.5
  • 12
    • 0032572866 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio- Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1998) Tetrahedron , vol.54 , pp. 10253
    • Yanagisawa, A.1    Kikuchi, T.2    Kuribayashi, T.3    Yamamoto, H.4
  • 13
    • 0001961783 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio- Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1998) J. Chem. Soc., Chem. Commun. , pp. 1573
    • Yanagisawa, A.1    Inanami, H.2    Yamamoto, H.3
  • 14
    • 0032486155 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio- Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1847
    • Aboulhoda, S.J.1    Reiners, I.2    Wilken, J.3    Henin, F.4    Martens, J.5    Muzart, J.6
  • 15
    • 0001935717 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio- Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1998) Synlett , pp. 607
    • Mikami, K.1    Yamaoka, M.2    Yoshida, A.3
  • 16
    • 0002284321 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio- Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1997) Synlett , pp. 411
    • Yanagisawa, A.1    Ishihara, K.2    Yamamoto, H.3
  • 17
    • 0030679752 scopus 로고    scopus 로고
    • (b) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. Asensio, G.; Cuenca, A.; Gavina, P.; Medio- Simon, M. Tetrahedron Lett. 1999, 40, 3939. Asensio, G.; Aleman, P.; Cuenca, A.; Gil, J.; Medio-Simon, M. Tetrahedron: Asymmetry 1998, 9, 4073. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. Asensio, G.; Aleman, P.; Gil, J.; Domingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Yanagisawa, A.; Inanami, H.; Yamamoto, H. J. Chem. Soc., Chem. Commun. 1998, 1573. Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7181
    • Martin, J.1    Lasne, M.-C.2    Plaquevent, J.-C.3    Duhamel, L.4
  • 18
    • 0000546293 scopus 로고
    • (c) Piva, O.; Mortezaei, R.; Henin, F.; Muzart, J.; Pete, J. P. J. Am. Chem. Soc. 1990, 112, 9263. Piva, O.; Pete, J. P. Tetrahedron Lett. 1990, 36, 5157. Henin, F.; Muzart, J.; Pete, J. P.; M'boungou-M'passi, A.; Rau, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 416. Muzart, J.; Henin, F.; Pete, J. P.; M'Boungou-M'Passi, A. Tetrahedron: Asymmetry 1993, 4, 2531.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 9263
    • Piva, O.1    Mortezaei, R.2    Henin, F.3    Muzart, J.4    Pete, J.P.5
  • 19
    • 0025150223 scopus 로고
    • (c) Piva, O.; Mortezaei, R.; Henin, F.; Muzart, J.; Pete, J. P. J. Am. Chem. Soc. 1990, 112, 9263. Piva, O.; Pete, J. P. Tetrahedron Lett. 1990, 36, 5157. Henin, F.; Muzart, J.; Pete, J. P.; M'boungou-M'passi, A.; Rau, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 416. Muzart, J.; Henin, F.; Pete, J. P.; M'Boungou-M'Passi, A. Tetrahedron: Asymmetry 1993, 4, 2531.
    • (1990) Tetrahedron Lett. , vol.36 , pp. 5157
    • Piva, O.1    Pete, J.P.2
  • 20
    • 33748225940 scopus 로고
    • (c) Piva, O.; Mortezaei, R.; Henin, F.; Muzart, J.; Pete, J. P. J. Am. Chem. Soc. 1990, 112, 9263. Piva, O.; Pete, J. P. Tetrahedron Lett. 1990, 36, 5157. Henin, F.; Muzart, J.; Pete, J. P.; M'boungou-M'passi, A.; Rau, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 416. Muzart, J.; Henin, F.; Pete, J. P.; M'Boungou-M'Passi, A. Tetrahedron: Asymmetry 1993, 4, 2531.
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 416
    • Henin, F.1    Muzart, J.2    Pete, J.P.3    M'Boungou-M'Passi, A.4    Rau, H.5
  • 21
    • 0027139307 scopus 로고
    • (c) Piva, O.; Mortezaei, R.; Henin, F.; Muzart, J.; Pete, J. P. J. Am. Chem. Soc. 1990, 112, 9263. Piva, O.; Pete, J. P. Tetrahedron Lett. 1990, 36, 5157. Henin, F.; Muzart, J.; Pete, J. P.; M'boungou-M'passi, A.; Rau, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 416. Muzart, J.; Henin, F.; Pete, J. P.; M'Boungou-M'Passi, A. Tetrahedron: Asymmetry 1993, 4, 2531.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 2531
    • Muzart, J.1    Henin, F.2    Pete, J.P.3    M'Boungou-M'Passi, A.4
  • 27
    • 0342747434 scopus 로고    scopus 로고
    • note
    • In a control experiment, (R)-34 (95% ee) was treated with the same ratio of diamine 1a + lithioamide 5 that would be present after enolate protonation in THF prior to workup. After 10 min at 0°C, the mixture was allowed to warm to 20°C and was then quenched in the usual way to give 4c with 31% ee, indicating partial racemization.
  • 30
    • 0025023939 scopus 로고
    • Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem. Pharm. Bull. 1981, 29, 1475. Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1990, 31, 5507.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5507
    • Aoyama, T.1    Shioiri, T.2
  • 31
    • 0342312537 scopus 로고    scopus 로고
    • note
    • A hydrazide corresponding to 7, but derived from N,N′-diisopropylhydrazine could also be deracemized. Because of the presence of an N-H subunit, a temporary blocking procedure was used as follows: N-H lithiation with 1 equiv of n-BuLi; N-silylation with TMSC1 (1 equiv) at -78°C; enolate formation with 2 equiv of n-BuLi; protonation with 1a, and quenching as usual. The recovered hydrazide after aqueous workup was formed with 69-72% ee.
  • 32
    • 0343617465 scopus 로고    scopus 로고
    • note
    • Prepared from the known carboxylic acids (ref 13) via the acid chloride and diisopropylamine; see the Experimental Section.
  • 39
    • 0342312523 scopus 로고    scopus 로고
    • note
    • The absolute configuration is assigned by analogy to (R)-10.
  • 42
    • 0343617460 scopus 로고    scopus 로고
    • note
    • Absolute configuration not assigned.
  • 45
    • 0000598748 scopus 로고
    • Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390. Hogeveen, H.; Zwart, L. Tetrahedron Lett. 1982, 23, 105.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 105
    • Hogeveen, H.1    Zwart, L.2
  • 48
    • 0342312516 scopus 로고    scopus 로고
    • note
    • 3 signal upfield relative to the E-isomer). The assignment was confirmed in the case of the enol silanes derived from 4a by an NOE experiment. In contrast to the major enol silanes derived from 4a and from 9b, the major enol silane isomer from 9a has a downfield chemical shift (δ 0.253 ppm, major, vs -0.122 ppm, minor), suggesting that this may be the E-enol silane 23a-E. A definitive assignment could not be made using NOE methods.
  • 49
    • 0343182080 scopus 로고    scopus 로고
    • note
    • This value was determined by Bordwell and Satish; see ref 7.
  • 50
    • 84990085779 scopus 로고
    • Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624. Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhayay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271.
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 1624
    • Seebach, D.1
  • 53
    • 0030500535 scopus 로고    scopus 로고
    • (a) Kresge, A. J. Chem. Soc. Rev. 1996, 25, 275. Kresge, A. J. Acc. Chem. Res. 1990, 23, 43.
    • (1996) Chem. Soc. Rev. , vol.25 , pp. 275
    • Kresge, A.J.1
  • 54
    • 0002905711 scopus 로고
    • (a) Kresge, A. J. Chem. Soc. Rev. 1996, 25, 275. Kresge, A. J. Acc. Chem. Res. 1990, 23, 43.
    • (1990) Acc. Chem. Res. , vol.23 , pp. 43
    • Kresge, A.J.1
  • 55
    • 0009673198 scopus 로고
    • (b) Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 93, 1007. Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694. Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
    • (1981) Angew. Chem. , vol.93 , pp. 1007
    • Seebach, D.1    Wasmuth, D.2
  • 56
    • 0345022255 scopus 로고
    • (b) Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 93, 1007. Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694. Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9694
    • Kawabata, T.1    Yahiro, K.2    Fuji, K.3
  • 57
    • 0001694916 scopus 로고    scopus 로고
    • (b) Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 93, 1007. Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694. Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
    • (1998) Chem. Eur. J. , vol.4 , pp. 373
    • Fuji, K.1    Kawabata, T.2
  • 58
    • 0030583467 scopus 로고    scopus 로고
    • (b) Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 93, 1007. Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694. Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373. Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7607
    • Hughes, A.D.1    Price, D.A.2    Shishkin, O.3    Simpkins, N.S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.