Reaction of lithio tert-butyl trimethylsilylacetate with aldehydes and ketones. A synthesis of α,β-unsaturated esters.
✍ Scribed by Stephen L. Hartzell; Donald F. Sullivan; Michael W. Rathke
- Publisher
- Elsevier Science
- Year
- 1974
- Tongue
- French
- Weight
- 164 KB
- Volume
- 15
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
received in UK for plblicrtian 4 Maroh 1974) Addition of tert-butyl trimethylsilylacetatel to tetrahydrofuran (THF) solutions of lithium diisopropylamide at -78' produces the lithimn ester enolate, I, (eq 1) as a white precipitate. Attempts to isolate I have been unsuccessful; however, suspensions of I in THF are stable
📜 SIMILAR VOLUMES
Stereoselective Conjugate Addition Reactions of α,β-Unsaturated tert-Butyl Esters with Aryllithium Reagents. -Aryllithium reagents undergo stereoselective 1,4-addition reactions to α,β-unsaturated tert-butyl esters bearing a chirally modified aryl substituent at C-3. Good selectivities are obtained
An addition of benzaldehyde to an ethereal solution of w-butyldimethylsilyldibromo methyllithium provided or-bromo-a-silyl ketone. Further treatment of the a-bmmoa-silyl ketone with butyllithium afforded enolate which provided g-hydroxya-silyl ketone upon treatment with aldehyde in ether. The enolat