Enantioselective aldol reactions catalyzed by tin methoxide and BINAP*Silver(I) complex [19]

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 892-893

  Yanagisawa, Akira ^a   Matsumoto, Yukari ^a   Asakawa, Kenichi ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SILVER;

CATALYSIS; CHEMICAL REACTION KINETICS; ENANTIOMER; LETTER; METAL BINDING; ORGANIC CHEMISTRY; REACTION ANALYSIS;

EID: 0033518596     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982857q     Document Type: Letter

References (32)

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13. 2b
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15. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
16. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
17. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
18. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
19. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
20. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
21. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
22. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
23. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
24. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
25. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
26. Examples of catalytic asymmetric aldol reactions with silyl enol ethers or ketene silyl acetals, reviews: (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570. (c) Braun, M. 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 1730. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (e) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137. Notable recent communications: (f) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341. (g) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837. (h) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918. Related catalytic asymmetric Mannich-type reactions: (i) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (j) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Examples of direct catalytic asymmetric aldol reactions of aldehydes with unmodified ketones: (k) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (l) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
27. Yanagisawa, A.; Matsumoto Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319.
28. Amberger, E.; Kula, M.-R.; Lorberth, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 138. See also: Jones, K.; Lappert, M. F. J. Organomet. Chem. 1965, 3, 295.
29. Amberger, E.; Kula, M.-R.; Lorberth, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 138. See also: Jones, K.; Lappert, M. F. J. Organomet. Chem. 1965, 3, 295.
30. Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
31. 4 and a catalytic amount (20 mol %) of chiral Schiff base, see: Oguni, N.; Tanaka, K.; Ishida, H. Synlett 1998, 601.
32. The reactivity of tributyltin methoxide (n = 1) toward diketene was low and the reaction required a temperature of more than 0°C as shown in equation a. (Formula Presented) n = 1 (-20°C, 1.5 h): <1% n = 1 (0°C ∼ r.t., 6 h): 12% n = 2 (-20°C, 4 h): 25% In contrast, under the influence of 10 mol % of dibutyltin dimethoxide (n = 2), the reaction was found to proceed catalytically even at -20°C and an aldol adduct was formed in 25% yield after 4 h of stirring.