Tandem aldol-reduction reaction of dimethylsilyl enolates: A new method for stereoselective preparation of 1,3-diols

Chemistry Letters

Volumn , Issue 2, 2000, Pages 150-151

  Miura, Katsukiyo ^a   Nakagawa, Takahiro ^a   Suda, Shuntaro ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034336001     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.150     Document Type: Article

References (24)

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4. Recent papers on 1,3-diol synthesis: a) N. A. Powell and S. D. Rychnovsky, J. Org. Chem., 64, 2026 (1999).
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8. Natural products including 1,3-diol unit: S. D. Rychnovsky, Chem. Rev., 95, 2021 (1995): R. D. Norcross and I. Paterson, Chem. Rev., 95, 2041 (1995); R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 26, 489 (1987).
9. Natural products including 1,3-diol unit: S. D. Rychnovsky, Chem. Rev., 95, 2021 (1995): R. D. Norcross and I. Paterson, Chem. Rev., 95, 2041 (1995); R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 26, 489 (1987).
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19. We also attempted the uncatalyzed reaction of 5 with benzaldehyde. However, it hardly afforded 1,3-diol 7 even at 100 °C.
20. a) R. Noyori, I. Nishida, and J. Sakata, J. Am. Chem. Soc., 105, 1598 (1983).
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23. 2O)-mediated reaction of 5 with benzaldehyde gave only 6 without 7, although it was known that a Lewis acid induced the intramolecular hydrosilylation of ketones. S. Anwar and A. P. Davis, J. Chem. Soc., Chem. Commun., 1986, 831. See also Ref. 6.
24. Fujita and Hiyama have reported that the fluoride ion-catalyzed intramolecular reduction of a β-(dimethylsilyloxy)ketone proceeds with moderate 1,3-anti-selectivity. See Ref. 13.