Enantioselective aldol reaction with bromofluoroketene silyl acetals

Tetrahedron

Volumn 55, Issue 8, 1999, Pages 2225-2236

  Iseki, Katsuhiko ^a   Kuroki, Yoshichika ^a   Kobayashi, Yoshiro ^a  

^a DAIKIN INDUSTRIES LTD   (Japan)

Author keywords

Aldehydes; Aldol reactions; Asymmetric synthesis; Fluorine and compounds

Indexed keywords

ACETAL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0033582499     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00005-8     Document Type: Article

References (20)

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10. Denmark et al. proposed that the boat-like transition states are extremely predominant in the uncatalyzed aldol reaction of enoxysilacyclobutanes and trichlorosilyl enolates. See: a) Denmark, S. E.; Griedel, B. D.; Coe, D. M.; Schnute, M. E. J. Am. Chem. Soc. 1994, 116, 7026-7043.
11. b) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334.
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14. A decrease in the amount of catalyst 5 (<10 mol%) dramatically suppressed the enantioselectivity.
15. W = 0.050).
16. Kuwajima, I.; Kato, M.; Mori, A. Tetrahedron Lett. 1980, 21, 4291-4294.
17. Mikami et al. proposed the silatropic ene mechanism for the asymmetric aldol reaction with ketene silyl acetals. See: a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078.
18. b) Mikami, K.; Matsukawa, S.; Sawa, E.; Harada, A.; Koga, N. Tetrahedron Lett. 1997, 38, 1951-1954.
19. The aldol reaction catalyzed by a bidentate Lewis acid was reported by Maruoka et al. See: Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307-11308.
20. Iseki, K.; Kuroki, Y.; Kobayashi, Y. Tetrahedron: Asymmetry 1998, 9, 2889-2894.