Asymmetric aldol addition of aldehydes to a difluoroketene silyl acetal catalyzed by chiral Lewis acids

Tetrahedron

Volumn 53, Issue 30, 1997, Pages 10271-10280

  Iseki, Katsuhiko ^a   Kuroki, Yoshichika ^a   Asada, Daisuke ^a   Takahashi, Mie ^a   Kishimoto, Satoshi ^a   Kobayashi, Yoshiro ^a  

^a DAIKIN INDUSTRIES LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOFLUORINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE;

EID: 0030873311     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00683-2     Document Type: Article

References (36)

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19. The difluoroketene silyl acetal 1 is considerably stable and can be stored at -20°C over several months.
20. The CAB catalyst developed by Yamamoto at al. (Furuta, K.; Maruyama, T.; Yamamoto, H. Synlett, 1991, 439-440 and references cited therein) and the BINOL-derived titanium complex of Mikami et al. (Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078 and references cited therein) were not effective for enamioselectivity.
21. The CAB catalyst developed by Yamamoto at al. (Furuta, K.; Maruyama, T.; Yamamoto, H. Synlett, 1991, 439-440 and references cited therein) and the BINOL-derived titanium complex of Mikami et al. (Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078 and references cited therein) were not effective for enamioselectivity.
22. 3·THF and p-toluenesulfonamide of the corresponding amino acid in nitroethane at 45°C for 1 h. See: a) Parmee, E.R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365-9366.
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30. Mikami et al. suggested the silatropic ene mechanism for the asymmetric catalysis of aldol-type reactions with ketene silyl acetals. See: a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077-4078.
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