Stereoselective aldol reactions of β-boronate carbonyl derivatives.
✍ Scribed by Anthony D.M. Curtis; Andrew Whiting
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 188 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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Ecient synthetic methods for 1,3-di-O-benzyldihydroxyacetone (3) and 1,3-O-cyclohexylidenedihydroxyacetone (8) were developed. TiCl 4 -mediated aldol reaction of the silyl enol ether of 3 with aldehydes gave syn aldol products while the reaction of the silyl enol ether of 8 with aldehydes aorded ant
## Abstract For Abstract see ChemInform Abstract in Full Text.
A study on the addition of boron enolates of methyl ketones to trans a,b-epoxy aldehydes is reported. The reaction proceeds with an excellent anti stereoselectivity, consistent with the Felkin-Ahn model, toward the synthesis of hydroxylated compounds with defined stereochemistry.