Ally1 enol carbonates, prepared by quenching ketone enolates with ally1 chloroformate, are converted to a,&unsaturated ketones with Pd(OAc)2-dppe catalyst in CH3CN.
Allyloxy ketone enol ether-claisen rearrangement. regiospecific synthesis of allyl ketones from allyl alcohols
β Scribed by Joseph L.C. Kachinski; Robert G. Salomon
- Publisher
- Elsevier Science
- Year
- 1977
- Tongue
- French
- Weight
- 212 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Claisen rearrangement of ally1 vinyl ethers is an important general method of carboncarbon bond formation for synthesis of y,b-unsaturated aldehydes and ketones. 1 Syntheses of y,b-unsaturated esters and amides are similarly achieved by rearrangements of 2-alkoxy and 2amino-3-oxa-1,5-hexadienes.
π SIMILAR VOLUMES
Fluoromethyl ketone enol ethers are regiospecifically prepared in good yields by treatment of 2-alkoxy-1,3-bis(t-butyldimethylsiloxy)alkane with TBAF-MsF, and subsequent thermal [ 3,3]-sigmatropic rearrangement on the 2-alkenyl enol ethers gives a-allylated products. A fluoromethyl ketone bearing a
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