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■ Reactions of 5,5-Dimethyl-4-methylene-1,3-dioxolan-2-one with Amines in the Presence of Palladium Catalyst

Min Shi,* Yu-Mei Shen, and Ya-Jun Chen

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 354 Finglin Lu, Shanghai 200032, China

Abstract

In the reaction of 5,5-dimethyl-4-methylene-1,3-dioxolan-2-one with primary amines in the presence of Pd(0) catalyst, the 3-alkyl-4-hydroxy-4,5,5-trimethyloxazolidin-2-ones (1) are obtained as the major products, along with the formation of ring opened products at room temperature. On the other hand, 3-alkyl-5,5-dimethyl-4-methyloxazolidin-2-ones (2) are obtained as reaction products in high yields at high temperature. But in the absence of Pd(0) catalyst, the ring opened compounds alkylcarbamic acid 1,1-dimethyl-2-oxopropyl esters (3) are formed exclusively. In addition, in the reaction of 5,5-dimethyl-4-methylene-1,3-dioxolan-2-one with secondary amines, the ring opened compounds were obtained as the sole products. A plausible mechanism for the formation of 1 and 2 is proposed.