Novel Route to Triethylsilyl-Substituted Cyclopropanes

Shi-Guang Li (1) , Samir Z. Zard (2)

1 School of Mathematical Sciences
2 DCSO - Laboratoire de synthèse organique

Radical adducts of S-α-ketonyl dithiocarbonates (xanthates) to triethyl vinylsilane are converted into triethylsilyl-substituted cyclopropanes upon ozonolysis followed by exposure to 1,4-dibromobutane and Cs2CO3/18-crown-6 in refluxing acetonitrile. The sequence works best with phenacyl type adducts, and the use of the less bulky trimethysilyl (TMS) derivatives results in extensive desilylation.

Domaines: Chimie organique

Shi-Guang Li, Samir Z. Zard. Novel Route to Triethylsilyl-Substituted Cyclopropanes. Organic Letters, 2014, 16 (23), pp.6180-6183. ⟨10.1021/ol503081b⟩. ⟨hal-01102507⟩