Y. Tominaga, K. Ogata, S. Kohra
Oct 14, 1991
Citations
0
Influential Citations
17
Citations
Journal
Tetrahedron Letters
Abstract
Abstract [3+2]cycloaddition; N-(trimethylsilylmethyl)isothiourea, synthetic equivalent; 1,3-dipolar reagent, iminoazomethine ylid N-(Trimethylsilylmethyl)isothioureas, readily prepared by the reaction of N-bis(methylthio)methylene-cyanamide or -p-toluenesulfonamide with (trimethylsilylmethyl)amine, followed by N-alkylation, have been found to be a synthetic equivalent of iminoazomethine ylid. Treatment of these compounds with cesium fluoride in the presence of reactive heterodipolarophiles such as carbonyl compounds afforded 1,3-dipolar cycloadducts, 2-imino-oxazolidines and 2-iminothiazolidines, via 1,3-elimination of (methylthio)trimethylsilane.