Uncatalyzed aldol reaction using a dimethylsilyl enolate and α- dimethylsilyl ester in N,N-dimethylformamide

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2585-2588

  Miura, Katsukiyo ^a   Sato, Hiroshi ^a   Tamaki, Kentaro ^a   Ito, Hajime ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

N,N DIMETHYLFORMAMIDE;

ARTICLE; CARBOXY TERMINAL SEQUENCE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ESTERIFICATION; HYDROGEN BOND; MOLECULAR INTERACTION; NONHUMAN; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0032560067     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00275-5     Document Type: Article

References (28)

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11. 4. Other uncatalyzed aldol reactions using silyl enolates: (a) Kita, Y.; Tamura, O.; Itoh, F.; Yasuda, H.; Kishino, H.; Ke, Y. Y.; Tamura, Y. J. Org. Chem. 1988, 53, 554-561.
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14. 5. The DMS enolates 1a-d could be readily prepared from the corresponding ketones by deprotonation with LDA followed by silylation with DMSCI. House, H. O.; Czuba, L. J.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1969, 34, 2324-2336.
15. 6. (a) Hexamethylphosphoramide (HMPA) promoted considerably the hydride reduction of carbonyl group to give 3a rather than the aldol reaction.
16. (b) The stereoselective synthesis of 1,3-diols by this reaction is under investigation. The Lewis-acid induced intramolecular hydrosilylation of ketone has been utilized for the synthesis of anti-1,3-diols. Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770.
17. 7. Kobayashi et al. have reported that the coordination of DMF to silicon is crucial for the allylation with allyltrichlorosilane, in which, however, a cyclic transition state is proposed from the stereochemical outcome. Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620-6628.
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21. 3 aq. provided only 7c in 16% isolated yield.
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