Enantioselective protonation of silyl enol ethers and ketene disilyl acetals with Lewis acid-assisted chiral Bronsted acids: Reaction scope and mechanistic insights

Journal of the American Chemical Society

Volumn 122, Issue 34, 2000, Pages 8120-8130

  Nakamura, Shingo ^a   Kaneeda, Masanobu ^a   Ishihara, Kazuaki ^b   Yamamoto, Hisashi ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; CARBONYL DERIVATIVE; KETONE DERIVATIVE; PROTON; SILANE DERIVATIVE; STANNIC CHLORIDE;

ARTICLE; CALCULATION; CATALYSIS; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; PROTON TRANSPORT; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0034734366     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001164i     Document Type: Article

References (105)

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2. Recent reviews: (a) Hünig, S. In Houben-Weyl: Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E 21, p 3851. (b) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. (c) Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411.
3. Recent reviews: (a) Hünig, S. In Houben-Weyl: Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E 21, p 3851. (b) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566. (c) Yanagisawa, A.; Ishihara, K.; Yamamoto, H. Synlett 1997, 411.
4. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
5. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
6. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
7. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
8. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
9. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
10. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
11. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
12. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
13. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
14. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
15. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
16. Recent reports: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175 and references therein. (b) Yanagisawa, A.; Kuribayashi, T.; Kikuchi, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 107. (c) Fuji, K.; Kawabata, T.; Kuroda, A. J. Org. Chem. 1995, 60, 1914 and references therein. (d) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891. (e) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293 and references therein. (f) Martin, J.; Lansne, M.-C.; Plaquevent, J.-C.; Duhamel, L. Tetrahedron Lett. 1997, 38, 7181. (g) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857 and references therein. (h) Yanagisawa, A.; Inanami, H.; Yamamoto, H. Chem. Commun. 1998, 1573. (i) Yanagisawa, A.; Kikuchi, T.; Yamamoto, H. Synlett 1998, 174. (j) Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253. (k) Part. L.; Mojovic, L.; Levacher, V.; Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron: Asymmetry 1998, 9, 2509. (l) Asensio, G.; Cuenca, A.; Gavina, P.; Medio-Simon, M. Tetrahedron Lett. 1999, 40, 3939 and references therein. (m) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Yamada, M.; Yoshida, A.; Mikami, K. Tetrahedron 1999, 55, 4595 and references therein.
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26. A study of protonolysis of silyl enol ethers carried out by Novice et al. indicated C-protonation in the case of tert-butyl dimethylsilyl enol ethers, while no conclusion was arrived at for trimethyl silyl enol ethers: Novice, M. H.; Seikaly, H. R.; Seiz, A. D.; Tidwell, T. T. J. Am. Chem. Soc. 1980, 102, 5835.
27. (a) Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179.
28. (b) Ishihara, K.; Nakamura, S.; Yamamoto, H. Croat. Chem. Acta 1996, 69, 513.
29. (c) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854.
30. (d) Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 6429.
31. The other LBA-related reports are listed: (a) Ishihara, K.; Ishida, Y.; Nakamura, S.; Yamamoto, H. Synlett 1997, 758. (b) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. (c) Ishihara, K.; Nakamura, S.; Yamamoto, H. J. Am. Chem. Soc. 1999, 121, 4906.
32. The other LBA-related reports are listed: (a) Ishihara, K.; Ishida, Y.; Nakamura, S.; Yamamoto, H. Synlett 1997, 758. (b) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. (c) Ishihara, K.; Nakamura, S.; Yamamoto, H. J. Am. Chem. Soc. 1999, 121, 4906.
33. The other LBA-related reports are listed: (a) Ishihara, K.; Ishida, Y.; Nakamura, S.; Yamamoto, H. Synlett 1997, 758. (b) Ishihara, K.; Nakamura, H.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444. (c) Ishihara, K.; Nakamura, S.; Yamamoto, H. J. Am. Chem. Soc. 1999, 121, 4906.
34. For references on regioselective preparation of thermodynamic silyl enol ethers, see: (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: San Diego, 1988; p 100. (b) Krafft, M. E.; Holton, R. A. Tetrahedron Lett. 1983, 24, 1345. (c) House, H. O.; Fischer, W. F., Jr.; Mclauglin, T. E.; Peet, N. P. J. Org. Chem. 1971, 36, 3429. (d) Zembayashi, M.; Tamao. K.; Kumada, M. Synthesis 1977, 422. (e) Emde, H.; Götz, A.; Hofmann, K.; Simchen, G. Liebigs Ann. Chem. 1981, 1643.
35. For references on regioselective preparation of thermodynamic silyl enol ethers, see: (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: San Diego, 1988; p 100. (b) Krafft, M. E.; Holton, R. A. Tetrahedron Lett. 1983, 24, 1345. (c) House, H. O.; Fischer, W. F., Jr.; Mclauglin, T. E.; Peet, N. P. J. Org. Chem. 1971, 36, 3429. (d) Zembayashi, M.; Tamao. K.; Kumada, M. Synthesis 1977, 422. (e) Emde, H.; Götz, A.; Hofmann, K.; Simchen, G. Liebigs Ann. Chem. 1981, 1643.
36. For references on regioselective preparation of thermodynamic silyl enol ethers, see: (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: San Diego, 1988; p 100. (b) Krafft, M. E.; Holton, R. A. Tetrahedron Lett. 1983, 24, 1345. (c) House, H. O.; Fischer, W. F., Jr.; Mclauglin, T. E.; Peet, N. P. J. Org. Chem. 1971, 36, 3429. (d) Zembayashi, M.; Tamao. K.; Kumada, M. Synthesis 1977, 422. (e) Emde, H.; Götz, A.; Hofmann, K.; Simchen, G. Liebigs Ann. Chem. 1981, 1643.
37. For references on regioselective preparation of thermodynamic silyl enol ethers, see: (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: San Diego, 1988; p 100. (b) Krafft, M. E.; Holton, R. A. Tetrahedron Lett. 1983, 24, 1345. (c) House, H. O.; Fischer, W. F., Jr.; Mclauglin, T. E.; Peet, N. P. J. Org. Chem. 1971, 36, 3429. (d) Zembayashi, M.; Tamao. K.; Kumada, M. Synthesis 1977, 422. (e) Emde, H.; Götz, A.; Hofmann, K.; Simchen, G. Liebigs Ann. Chem. 1981, 1643.
38. For references on regioselective preparation of thermodynamic silyl enol ethers, see: (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: San Diego, 1988; p 100. (b) Krafft, M. E.; Holton, R. A. Tetrahedron Lett. 1983, 24, 1345. (c) House, H. O.; Fischer, W. F., Jr.; Mclauglin, T. E.; Peet, N. P. J. Org. Chem. 1971, 36, 3429. (d) Zembayashi, M.; Tamao. K.; Kumada, M. Synthesis 1977, 422. (e) Emde, H.; Götz, A.; Hofmann, K.; Simchen, G. Liebigs Ann. Chem. 1981, 1643.
39. 8a that the enantioselectivity was incresed by using the sterically bulky trialkylsilyl group such as tert-butyldimethylsilyl group is incorrect.
40. (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: San Diego, 1988; p 102.
41. (b) Alinaworth, C.; Kuo, Y.-N. J. Organomet. Chem. 1972, 46, 73.
42. (c) Kuo, Y.-N.; Chen, F.; Ainaworth, C. J. Chem. Soc., Chem. Commun. 1971, 136.
43. (d) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: San Diego, 1988; p 77.
44. For a recent review of Profen drugs, see: Stahly, G. P.; Starrett, R. M. In Chirality in Industry II; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; Wiley: Chichester, 1997; pp 17-40.
45. (a) Schlama, T.; Baati, R.; Gouverneur, V.; Valleix, A.; Falck, J. R.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1998, 37, 2085.
46. (b) Murai, A. In Comprehensive Natural Products Chemistry; Sir Derek, D., Nakanishi, K., Meth-Cohen, O., Sankawa, U., Eds.; Elsevier Science Ltd.: Oxford, 1999; Vol. 1, p 303.
47. Recent reports: (a) Angibaud, A.; Caumette, J. L.; Desmurs, J. R.; Duhamel, L.; Plé, G.; Valnot, J. Y.; Duhamel, P. Tetrahedron; Asymmetry 1995, 6, 1919. (b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011. (c) Oppolzer, W. Pure. Appl. Chem. 1990, 62, 1241. (d) Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799. (e) Sabiri, M.; Shao, L.; Sakurai, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 7877. (f) Kalaritis, P.; Regenye, R. W. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 258. (g) Koppenhoefer, B.; Schurig, V. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 119. (h) Fritz-Langhals, E.; Schütz, G. Tetrahedron Lett. 1993, 34, 293. (i) Giordano, C.; Coppi, L.; Restelli, A. J. Org. Chem. 1990, 55, 5400.
48. Recent reports: (a) Angibaud, A.; Caumette, J. L.; Desmurs, J. R.; Duhamel, L.; Plé, G.; Valnot, J. Y.; Duhamel, P. Tetrahedron; Asymmetry 1995, 6, 1919. (b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011. (c) Oppolzer, W. Pure. Appl. Chem. 1990, 62, 1241. (d) Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799. (e) Sabiri, M.; Shao, L.; Sakurai, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 7877. (f) Kalaritis, P.; Regenye, R. W. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 258. (g) Koppenhoefer, B.; Schurig, V. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 119. (h) Fritz-Langhals, E.; Schütz, G. Tetrahedron Lett. 1993, 34, 293. (i) Giordano, C.; Coppi, L.; Restelli, A. J. Org. Chem. 1990, 55, 5400.
49. Recent reports: (a) Angibaud, A.; Caumette, J. L.; Desmurs, J. R.; Duhamel, L.; Plé, G.; Valnot, J. Y.; Duhamel, P. Tetrahedron; Asymmetry 1995, 6, 1919. (b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011. (c) Oppolzer, W. Pure. Appl. Chem. 1990, 62, 1241. (d) Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799. (e) Sabiri, M.; Shao, L.; Sakurai, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 7877. (f) Kalaritis, P.; Regenye, R. W. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 258. (g) Koppenhoefer, B.; Schurig, V. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 119. (h) Fritz-Langhals, E.; Schütz, G. Tetrahedron Lett. 1993, 34, 293. (i) Giordano, C.; Coppi, L.; Restelli, A. J. Org. Chem. 1990, 55, 5400.
50. Recent reports: (a) Angibaud, A.; Caumette, J. L.; Desmurs, J. R.; Duhamel, L.; Plé, G.; Valnot, J. Y.; Duhamel, P. Tetrahedron; Asymmetry 1995, 6, 1919. (b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011. (c) Oppolzer, W. Pure. Appl. Chem. 1990, 62, 1241. (d) Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799. (e) Sabiri, M.; Shao, L.; Sakurai, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 7877. (f) Kalaritis, P.; Regenye, R. W. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 258. (g) Koppenhoefer, B.; Schurig, V. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 119. (h) Fritz-Langhals, E.; Schütz, G. Tetrahedron Lett. 1993, 34, 293. (i) Giordano, C.; Coppi, L.; Restelli, A. J. Org. Chem. 1990, 55, 5400.
51. Recent reports: (a) Angibaud, A.; Caumette, J. L.; Desmurs, J. R.; Duhamel, L.; Plé, G.; Valnot, J. Y.; Duhamel, P. Tetrahedron; Asymmetry 1995, 6, 1919. (b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011. (c) Oppolzer, W. Pure. Appl. Chem. 1990, 62, 1241. (d) Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799. (e) Sabiri, M.; Shao, L.; Sakurai, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 7877. (f) Kalaritis, P.; Regenye, R. W. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 258. (g) Koppenhoefer, B.; Schurig, V. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 119. (h) Fritz-Langhals, E.; Schütz, G. Tetrahedron Lett. 1993, 34, 293. (i) Giordano, C.; Coppi, L.; Restelli, A. J. Org. Chem. 1990, 55, 5400.
52. Recent reports: (a) Angibaud, A.; Caumette, J. L.; Desmurs, J. R.; Duhamel, L.; Plé, G.; Valnot, J. Y.; Duhamel, P. Tetrahedron; Asymmetry 1995, 6, 1919. (b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011. (c) Oppolzer, W. Pure. Appl. Chem. 1990, 62, 1241. (d) Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799. (e) Sabiri, M.; Shao, L.; Sakurai, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 7877. (f) Kalaritis, P.; Regenye, R. W. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 258. (g) Koppenhoefer, B.; Schurig, V. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 119. (h) Fritz-Langhals, E.; Schütz, G. Tetrahedron Lett. 1993, 34, 293. (i) Giordano, C.; Coppi, L.; Restelli, A. J. Org. Chem. 1990, 55, 5400.
53. Recent reports: (a) Angibaud, A.; Caumette, J. L.; Desmurs, J. R.; Duhamel, L.; Plé, G.; Valnot, J. Y.; Duhamel, P. Tetrahedron; Asymmetry 1995, 6, 1919. (b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011. (c) Oppolzer, W. Pure. Appl. Chem. 1990, 62, 1241. (d) Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799. (e) Sabiri, M.; Shao, L.; Sakurai, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 7877. (f) Kalaritis, P.; Regenye, R. W. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 258. (g) Koppenhoefer, B.; Schurig, V. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 119. (h) Fritz-Langhals, E.; Schütz, G. Tetrahedron Lett. 1993, 34, 293. (i) Giordano, C.; Coppi, L.; Restelli, A. J. Org. Chem. 1990, 55, 5400.
54. Recent reports: (a) Angibaud, A.; Caumette, J. L.; Desmurs, J. R.; Duhamel, L.; Plé, G.; Valnot, J. Y.; Duhamel, P. Tetrahedron; Asymmetry 1995, 6, 1919. (b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011. (c) Oppolzer, W. Pure. Appl. Chem. 1990, 62, 1241. (d) Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799. (e) Sabiri, M.; Shao, L.; Sakurai, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 7877. (f) Kalaritis, P.; Regenye, R. W. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 258. (g) Koppenhoefer, B.; Schurig, V. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 119. (h) Fritz-Langhals, E.; Schütz, G. Tetrahedron Lett. 1993, 34, 293. (i) Giordano, C.; Coppi, L.; Restelli, A. J. Org. Chem. 1990, 55, 5400.
55. Recent reports: (a) Angibaud, A.; Caumette, J. L.; Desmurs, J. R.; Duhamel, L.; Plé, G.; Valnot, J. Y.; Duhamel, P. Tetrahedron; Asymmetry 1995, 6, 1919. (b) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011. (c) Oppolzer, W. Pure. Appl. Chem. 1990, 62, 1241. (d) Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799. (e) Sabiri, M.; Shao, L.; Sakurai, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 7877. (f) Kalaritis, P.; Regenye, R. W. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 258. (g) Koppenhoefer, B.; Schurig, V. Organic Syntheses; Wiley: New York, Collect. Vol. VIII, 119. (h) Fritz-Langhals, E.; Schütz, G. Tetrahedron Lett. 1993, 34, 293. (i) Giordano, C.; Coppi, L.; Restelli, A. J. Org. Chem. 1990, 55, 5400.
56. (a) Hanna, M. W. J. Am. Chem. Soc. 1968, 90, 285.
57. (b) Hanna, M. W.; Williams, D. E. J. Am. Chem. Soc. 1968, 90, 5358.
58. (c) Cook, E. G., Jr.; Schug, J. C. J. Chem. Phys. 1970, 53, 723.
59. (d) Schug, J. C.; Dyson, M. C. J. Chem. Phys. 1973, 58, 297.
60. Although silyl enol ethers derived from 2-chlorocycloheptanone and 2-chlorocyclopentanone were also examined for the reaction, their ee values were only moderate.
61. (a) Barrelle, M.; Hamman, S. J. Chem. Res. (S) 1995, 317.
62. (b) Hamman, S.; Barrelle, M.; Tetaz, F.; Beguin, J. J. Fluorine Chem. 1987, 37, 85.
63. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
64. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
65. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
66. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
67. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
68. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
69. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
70. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
71. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
72. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
73. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
74. For recent studies on the catalytic enantioselective protonation, see: (a) Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C.; Behnen, W.; Martens, J.; Mehler, T. Tetrahedron: Asymmetry 1994, 5, 1321. (b) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1888. (c) Yanagisawa, A.; Kikuchi, T.; Watanabe, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1995, 372. (d) Nakamura, Y.; Takeuchi, S.; Ohira, A.; Ohgo, Y. Tetrahedron Lett. 1996, 37, 2805. (e) Sugiura, M.; Nakai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2366. (f) Muzart, F.; Hénin, S.; Aboulhoda, J. Tetrahedron: Asymmetry 1997, 8, 381. (g) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589. (h) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Synlett 1997, 956. (i) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691. (J) Vedejs, E.; Kruger, A. W. J. Org. Chem. 1974, 39, 8691. (k) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847. (l) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
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