e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521
Silicon in organic synthesis. 23. Chloro [(trimethylsilyl) methyl] ketene as a useful intermediate for the elaboration of. alpha.-methylenecyclobutanones and- …
LA Paquette, RS Valpey, GD Annis
Index: Paquette, Leo A.; Valpey, Richard S.; Annis, Gary D. Journal of Organic Chemistry, 1984 , vol. 49, p. 1317 - 1319
Summary: The title ketene, which is readily available by dehydrohalogention of the a-chloro acid chloride, adds to cyclopentadiene, vinyl ethers, and silyl enol ethers to give cyclobutanones with complete stereocontrol (and regiocontrol where relevant). These products enter regiospecifically into ring expansion with diazomethane. Both sets of molecules experience desilylative elimination with introduction of an a-methylene group ...
![(1R,5R,7R)-7-chloro-1-hydroxy-7-((trimethylsilyl)methyl)bicyclo[3.2.0]heptan-6-one Structure](https://image.chemsrc.com/caspic/102/89121-59-5.png)
![5-hydroxy-6-methylidenebicyclo[3.2.0]heptan-7-one Structure](https://image.chemsrc.com/caspic/030/89121-70-0.png)
![(1R,5R,7R)-7-chloro-7-((trimethylsilyl)methyl)-1-((trimethylsilyl)oxy)bicyclo[3.2.0]heptan-6-one Structure](https://image.chemsrc.com/caspic/395/89121-69-7.png)