Tandem aldol-allylation reactions: Double C-C bond formation using silicon-tethered dinucleophiles

Tetrahedron Letters

Volumn 40, Issue 11, 1999, Pages 2183-2186

  Frost, Lisa M ^a   Smith, Julian D ^b   Berrisford, David J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

Acetals; Aldol reactions; Allylation; Silicon and compounds

Indexed keywords

ACETAL DERIVATIVE; ALLYL ALCOHOL; ALLYL COMPOUND; SILICONE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DIASTEREOISOMER; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033548565     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02126-1     Document Type: Article

References (22)

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10. Frost, L.M., Smith, J.D, Berrisford, D.J., unpublished results. All compounds reported herein are racemic.
11. House, H.O., Czuba, L.J., Gall, M., Olmstead, H.D., J. Org. Chem. 1969, 54, 2324-2336.
12. 2) afford only the aldol products, e.g. 21. In contrast, reactions of aldehydes with tethered silane 22 give homoallylic alcohols, e.g. 23, as the sole products. (formula presented)
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14. The anion may be associated with the silicon but is omitted for clarity. Similar intermediates in aldol reactions have been proposed in the literature: a) Hollis, T.K., Bosnich, B.,J. Am. Chem. Soc. 1995, 117, 4570-4581;
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19. 2: hexane/ethyl acetate 4/1 v/v). The compounds were fully characterised by standard analytical techniques. The stereochemistry of 10 was assigned by comparison of the n.m.r. spectra with the literature (Hoffmann, R., Brückner, R., Chem. Ber. 1992, 127, 1471-1484).
20. Aldehyde 19 is unstable to the reaction conditions. In contrast, no degradation products are observed using 9 (conditions as Table 1), suggesting that free aldehydes are not intermediates in the tandem reactions.
21. We note the recent preparation and application of dialkylsilyl enol ethers by Hosomi (Miura, K., Sato, H., Tamaki, K., Ito, H., Hosomi, A., Tetrahedron Lett. 1998, 39, 2585-2589). These undergo aldol reactions in the absence of Lewis acids and the resulting β-siloxyketones are known precusors to anti-1,3-diols (Anwar, S., Bradley, G., Davis, A.P., J. Chem. Soc. Perkin Trans. 1 1991, 1383-1389).
22. We note the recent preparation and application of dialkylsilyl enol ethers by Hosomi (Miura, K., Sato, H., Tamaki, K., Ito, H., Hosomi, A., Tetrahedron Lett. 1998, 39, 2585-2589). These undergo aldol reactions in the absence of Lewis acids and the resulting β-siloxyketones are known precusors to anti-1,3-diols (Anwar, S., Bradley, G., Davis, A.P., J. Chem. Soc. Perkin Trans. 1 1991, 1383-1389).