The Makaiyama type aldel reaction of his trimcthylsilyl ketene acetals 3 was investigated under high pressure conditions. Silyl aldois $ were oblained with a syn stereoselectivity, signifa?antly correlated upon the stedc bulk of R substitnent. In the case of unsaturated bis trimethylsilyl ketene ace
Ketene bis(trimethylsilyl) acetals. Cross-aldol condensation with aldehydes. Stereochemistry of the reaction
β Scribed by Jacques-Emile Dubois; Georges Axiotis; Emmanuel Bertounesque
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 270 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
enolsilanes 1 does not govern the stereochemistry of aldol condensation products. We recently reported for the first time', acetals la6'8, that compounds 2, structural analogous of add to aldehydes and Schiff bases in a cross-aldol type condensation, to afford B-hydroxyacids and B-Lactams respectively, with good yields. Continuing our investigations in this field, we report in this paper the stereochemical outcome of the reaction of enolate pro-chira1 equivalents Ib with aldehydes in the presente of titanium tetrachloride. This study makes -
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The title reaction with unsubstifufed and monosubstituted silyf ketene acetals proceeds with high enantioseiectivify, and in the latter case good dinstereoselecfivity favoring the anfi-/Chydrory-amethyl esters in all reported cases.