Diastereoselective aldol reaction of tin enolate of cyclohexanone catalyzed by metal triflates

Synlett

Volumn , Issue 9, 1998, Pages 958-960

  Yanagisawa, Akira ^a   Kimura, Kazutaka ^a   Nakatsuka, Yoshinari ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002793158     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-5737     Document Type: Article

References (30)

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3. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
4. (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.
5. (d) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
6. Recent communications: (e) 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.
7. (f) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
8. (g) Denmark, S. E.; Stavenger, R. A. J. Org. Chem. 1998, 63, 918.
9. Reviews: (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987; p 286.
10. (b) Davies, A. G. Organotin Chemistry; VCH: Weinheim, 1997; p 185.
11. The first example of catalytic enantioselective aldol addition of tributyltin enolates to aldehydes: (c) Yanagisawa, A.; Matsumoto Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319.
12. (a) Pereyre, M.; Bellegarde, B.; Mendelsohn, J.; Valade, J. J. Organomet. Chem. 1968, 11, 97.
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15. (a) Shenvi, S.; Stille, J. K. Tetrahedron Lett. 1982, 23, 627.
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18. See also: (d) Yamamoto, Y.; Yatagai, H.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1981, 162.
19. 2 and its complexes with phosphines: Murata, S.; Ido, Y. Bull. Chem. Soc. Jpn. 1994, 67, 1746.
20. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
21. Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500.
22. Good enantioselectivity has been observed for the BINAP-Pd(II) complex-catalyzed aldol reaction of silyl enol ethers with aldehydes: (a) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
23. (b) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463.
24. (a) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814.
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26. (c) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893.
27. 3) δ 24.5, 27.6, 30.6, 42.4, 57.3, 74.5, 126.9 (2 C), 127.7, 128.3 (2 C), 140.9, 215.3.
28. 3c
29. 3) δ 24.5, 27.5, 30.4, 42.4, 56.0, 72.8, 126.3 (2 C), 127.5, 128.3 (2 C), 128.8, 131.8, 136.4, 214.7.
30. 3-Cu(OTf)2 and related complexes are effective chiral catalysts for enantioselective aldol additions of silylketene acetals to α-(benzyloxy)acetaldehyde or pyruvate esters, see ref. 10.