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Volumn 65, Issue 10, 2000, Pages 2979-2983

Catalytic enantioselective protonation of lithium enolates with chiral imides

Author keywords

[No Author keywords available]

Indexed keywords

IMIDE; LITHIUM DERIVATIVE;

EID: 0034685934     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991565k     Document Type: Article
Times cited : (39)

References (72)
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    • Nakamura, Y.1    Takeuchi, S.2    Ohgo, Y.3    Yamaoka, M.4    Yoshida, A.5    Mikami, K.6
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    • Recent reports: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709. (b) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (e) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (f) Asensio, G.; Alemán, P. A.; Domingo, L. R.; Medio-Simón, M. Tetrahedron Lett. 1998, 39, 3277. (g) Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. (h) Asensio, G.; Alemán, P. A.; Gil, J.; Domingo, L. R.; Medio-Simón, M. J. Org. Chem. 1998, 63, 9342. Asensio, G.; Alemán, P. A.; Cuenca, A.; Gil, J.; Medio-Simón, M. Tetrahedron: Asymmetry 1998, 9, 4073. (j) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. (k) Asensio, G.; Cuenca, A.; Gaviña, P.; Medio-Simón, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1997) Chem. Commun. , pp. 1857
    • Kosugi, H.1    Abe, M.2    Hatsuda, R.3    Uda, H.4    Kato, M.5
  • 8
    • 0030839482 scopus 로고    scopus 로고
    • Recent reports: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709. (b) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (e) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (f) Asensio, G.; Alemán, P. A.; Domingo, L. R.; Medio-Simón, M. Tetrahedron Lett. 1998, 39, 3277. (g) Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. (h) Asensio, G.; Alemán, P. A.; Gil, J.; Domingo, L. R.; Medio-Simón, M. J. Org. Chem. 1998, 63, 9342. Asensio, G.; Alemán, P. A.; Cuenca, A.; Gil, J.; Medio-Simón, M. Tetrahedron: Asymmetry 1998, 9, 4073. (j) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. (k) Asensio, G.; Cuenca, A.; Gaviña, P.; Medio-Simón, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6861
    • Kosugi, H.1    Hoshino, K.2    Uda, H.3
  • 9
    • 0030679752 scopus 로고    scopus 로고
    • Recent reports: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709. (b) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (e) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (f) Asensio, G.; Alemán, P. A.; Domingo, L. R.; Medio-Simón, M. Tetrahedron Lett. 1998, 39, 3277. (g) Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. (h) Asensio, G.; Alemán, P. A.; Gil, J.; Domingo, L. R.; Medio-Simón, M. J. Org. Chem. 1998, 63, 9342. Asensio, G.; Alemán, P. A.; Cuenca, A.; Gil, J.; Medio-Simón, M. Tetrahedron: Asymmetry 1998, 9, 4073. (j) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. (k) Asensio, G.; Cuenca, A.; Gaviña, P.; Medio-Simón, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7181
    • Martin, J.1    Lasne, M.-C.2    Plaquevent, J.-C.3    Duhamel, L.4
  • 10
    • 0030717149 scopus 로고    scopus 로고
    • Recent reports: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709. (b) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (e) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (f) Asensio, G.; Alemán, P. A.; Domingo, L. R.; Medio-Simón, M. Tetrahedron Lett. 1998, 39, 3277. (g) Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. (h) Asensio, G.; Alemán, P. A.; Gil, J.; Domingo, L. R.; Medio-Simón, M. J. Org. Chem. 1998, 63, 9342. Asensio, G.; Alemán, P. A.; Cuenca, A.; Gil, J.; Medio-Simón, M. Tetrahedron: Asymmetry 1998, 9, 4073. (j) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. (k) Asensio, G.; Cuenca, A.; Gaviña, P.; Medio-Simón, 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
  • 11
    • 0032516320 scopus 로고    scopus 로고
    • Recent reports: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709. (b) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (e) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (f) Asensio, G.; Alemán, P. A.; Domingo, L. R.; Medio-Simón, M. Tetrahedron Lett. 1998, 39, 3277. (g) Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. (h) Asensio, G.; Alemán, P. A.; Gil, J.; Domingo, L. R.; Medio-Simón, M. J. Org. Chem. 1998, 63, 9342. Asensio, G.; Alemán, P. A.; Cuenca, A.; Gil, J.; Medio-Simón, M. Tetrahedron: Asymmetry 1998, 9, 4073. (j) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. (k) Asensio, G.; Cuenca, A.; Gaviña, P.; Medio-Simón, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3277
    • Asensio, G.1    Alemán, P.A.2    Domingo, L.R.3    Medio-Simón, M.4
  • 12
    • 0001935717 scopus 로고    scopus 로고
    • Recent reports: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709. (b) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (e) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (f) Asensio, G.; Alemán, P. A.; Domingo, L. R.; Medio-Simón, M. Tetrahedron Lett. 1998, 39, 3277. (g) Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. (h) Asensio, G.; Alemán, P. A.; Gil, J.; Domingo, L. R.; Medio-Simón, M. J. Org. Chem. 1998, 63, 9342. Asensio, G.; Alemán, P. A.; Cuenca, A.; Gil, J.; Medio-Simón, M. Tetrahedron: Asymmetry 1998, 9, 4073. (j) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. (k) Asensio, G.; Cuenca, A.; Gaviña, P.; Medio-Simón, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1998) Synlett , pp. 607
    • Mikami, K.1    Yamaoka, M.2    Yoshida, A.3
  • 13
    • 0032509250 scopus 로고    scopus 로고
    • Recent reports: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709. (b) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (e) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (f) Asensio, G.; Alemán, P. A.; Domingo, L. R.; Medio-Simón, M. Tetrahedron Lett. 1998, 39, 3277. (g) Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. (h) Asensio, G.; Alemán, P. A.; Gil, J.; Domingo, L. R.; Medio-Simón, M. J. Org. Chem. 1998, 63, 9342. Asensio, G.; Alemán, P. A.; Cuenca, A.; Gil, J.; Medio-Simón, M. Tetrahedron: Asymmetry 1998, 9, 4073. (j) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. (k) Asensio, G.; Cuenca, A.; Gaviña, P.; Medio-Simón, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1998) J. Org. Chem. , vol.63 , pp. 9342
    • Asensio, G.1    Alemán, P.A.2    Gil, J.3    Domingo, L.R.4    Medio-Simón, M.5
  • 14
    • 0032573446 scopus 로고    scopus 로고
    • Recent reports: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709. (b) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (e) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (f) Asensio, G.; Alemán, P. A.; Domingo, L. R.; Medio-Simón, M. Tetrahedron Lett. 1998, 39, 3277. (g) Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. (h) Asensio, G.; Alemán, P. A.; Gil, J.; Domingo, L. R.; Medio-Simón, M. J. Org. Chem. 1998, 63, 9342. Asensio, G.; Alemán, P. A.; Cuenca, A.; Gil, J.; Medio-Simón, M. Tetrahedron: Asymmetry 1998, 9, 4073. (j) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. (k) Asensio, G.; Cuenca, A.; Gaviña, P.; Medio-Simón, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 4073
    • Asensio, G.1    Alemán, P.A.2    Cuenca, A.3    Gil, J.4    Medio-Simón, M.5
  • 15
    • 0033538074 scopus 로고    scopus 로고
    • Recent reports: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709. (b) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (e) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (f) Asensio, G.; Alemán, P. A.; Domingo, L. R.; Medio-Simón, M. Tetrahedron Lett. 1998, 39, 3277. (g) Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. (h) Asensio, G.; Alemán, P. A.; Gil, J.; Domingo, L. R.; Medio-Simón, M. J. Org. Chem. 1998, 63, 9342. Asensio, G.; Alemán, P. A.; Cuenca, A.; Gil, J.; Medio-Simón, M. Tetrahedron: Asymmetry 1998, 9, 4073. (j) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. (k) Asensio, G.; Cuenca, A.; Gaviña, P.; Medio-Simón, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1999) Tetrahedron , vol.55 , pp. 4595
    • Nakamura, Y.1    Takeuchi, S.2    Ohgo, Y.3    Yamaoka, M.4    Yoshida, A.5    Mikami, K.6
  • 16
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    • Recent reports: (a) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron Lett. 1997, 38, 2709. (b) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857. Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861. Martin, J.; Lasne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (e) Tsunoda, T.; Kaku, H.; Nagaku, M.; Okuyama, E. Tetrahedron Lett. 1997, 38, 7759. (f) Asensio, G.; Alemán, P. A.; Domingo, L. R.; Medio-Simón, M. Tetrahedron Lett. 1998, 39, 3277. (g) Mikami, K.; Yamaoka, M.; Yoshida, A. Synlett 1998, 607. (h) Asensio, G.; Alemán, P. A.; Gil, J.; Domingo, L. R.; Medio-Simón, M. J. Org. Chem. 1998, 63, 9342. Asensio, G.; Alemán, P. A.; Cuenca, A.; Gil, J.; Medio-Simón, M. Tetrahedron: Asymmetry 1998, 9, 4073. (j) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamaoka, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595. (k) Asensio, G.; Cuenca, A.; Gaviña, P.; Medio-Simón, M. Tetrahedron Lett. 1999, 40, 3939.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3939
    • Asensio, G.1    Cuenca, A.2    Gaviña, P.3    Medio-Simón, M.4
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    • Enantioselective protonation of silyl enol ethers and ketene silyl acetals: (a) Cavelier, F.; Gomez, S.; Jacquier, R.; Verducci, J. Tetrahedron: Asymmetry 1993, 4, 2501. (b) Cavelier, F.; Gomez, S.; Jacquier, R.; Verducci, J. Tetrahedron Lett. 1994, 35, 2891. Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179. (d) Ishihara, K.; Nakamura, S.; Yamamoto, H. Croat. Chem. Acta 1996, 69, 513. (e) Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 6429. (f) Takahashi, M.; Ogasawara, K. Tetrahedron: Asymmetry 1997, 8, 3125.
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    • For examples of simple enolates, see: (a) Hogeveen, H.; Zwart, L. Tetrahedron Lett. 1982, 23, 105. (b) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1986, 27, 631. Matsumoto, K.; Ohta, H. Tetrahedron Lett. 1991, 32, 4729. Takahashi, T.; Nakao, N.; Koizumi, T. Chem. Lett. 1996, 207. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293.
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    • For examples of simple enolates, see: (a) Hogeveen, H.; Zwart, L. Tetrahedron Lett. 1982, 23, 105. (b) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1986, 27, 631. Matsumoto, K.; Ohta, H. Tetrahedron Lett. 1991, 32, 4729. Takahashi, T.; Nakao, N.; Koizumi, T. Chem. Lett. 1996, 207. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293.
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    • Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. Previous to our reports shown above, Rebek and co-workers had reported an asymmetric protonation of enolates using structurally related chiral lactams as chiral proton sources derived from Kemp's tricarboxylic acid:
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    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
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    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
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    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1995) Tetrahedron: Asymmetry , vol.8 , pp. 1865
    • Aboulhoda, S.J.1    Létinois, S.2    Wilken, J.3    Reiners, I.4    Hénin, F.5    Martens, J.6    Muzart, J.7
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    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1998) Tetrahedron Lett. , vol.37 , pp. 2805
    • Nakamura, Y.1    Takeuchi, S.2    Ohira, A.3    Ohgo, Y.4
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    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 12854
    • Ishihara, K.1    Nakamura, S.2    Kaneeda, M.3    Yamamoto, H.4
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    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 381
    • Muzart, J.1    Hénin, F.2    Aboulhoda, S.J.3
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    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2366
    • Sugiura, M.1    Nakai, T.2
  • 56
    • 0030795094 scopus 로고    scopus 로고
    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7589
    • Riviere, P.1    Koga, K.2
  • 57
    • 0001577626 scopus 로고    scopus 로고
    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1998) J. Org. Chem. , vol.63 , pp. 2792
    • Vedejs, E.1    Kruger, A.W.2
  • 58
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    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1847
    • Aboulhoda, S.J.1    Reiners, I.2    Wilken, J.3    Hénin, F.4    Martens, J.5    Muzart, J.6
  • 59
    • 0001005279 scopus 로고    scopus 로고
    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1998) J. Org. Chem. , vol.63 , pp. 6444
    • Ishihara, K.1    Nakamura, H.2    Nakamura, S.3    Yamamoto, H.4
  • 60
    • 0032547976 scopus 로고    scopus 로고
    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1998) , vol.39 , pp. 8691
    • Takeuchi, S.1    Nakamura, Y.2    Ohgo, Y.3    Tetrahedron Lett, C.D.P.4
  • 61
    • 0032577033 scopus 로고    scopus 로고
    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4043
    • Emori, E.1    Arai, T.2    Sasai, H.3    Shibasaki, M.4
  • 62
    • 0033599548 scopus 로고    scopus 로고
    • Other studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (b) Fehr, C.; Galindo, J. Helv. Chim. Acta 1995, 78, 539. (c) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 8, 1865. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1998, 37, 2805. (e) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854. (f) Muzart, J.; Hénin, F.; Aboulhoda, S. J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (h) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. Vedejs, E.; Kruger, A. W. J. Org. Chem. 1998, 63, 2792. (j) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (k) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. See also: Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043. (n) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2637
    • Hodous, B.L.1    Ruble, J.C.2    Fu, G.C.3
  • 63
    • 0003601534 scopus 로고    scopus 로고
    • Merck & Co. Inc.: Rahway, NJ
    • a value of succinimide is 9.5; see: The Merck Index, 12th ed.; Merck & Co. Inc.: Rahway, NJ, 1996; p 1515.
    • (1996) The Merck Index, 12th Ed. , pp. 1515
  • 64
    • 0004095340 scopus 로고
    • Butterworth: London
    • n-BuLi can be used for cleavage of the Si-O bond of silyl enol ether 7 instead of MeLi. Generation of lithium enolates: Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981; p 217.
    • (1981) Silicon in Organic Synthesis , pp. 217
    • Colvin, E.W.1
  • 65
    • 0342998435 scopus 로고    scopus 로고
    • note
    • a = ca. 8).
  • 66
    • 0343869752 scopus 로고    scopus 로고
    • note
    • 7a,b In contrast, the present protonation was performed in the absence of LiBr, and thus, a lower ee was observed.


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