含硫碳负离子的反应及其应用的研究(Ⅰ)——固-液相转移催化法合成取代肉桂酸酯

Studies on Some Reactions of Sulfur-Containing Carbanions and Their Synthetic Applications (Ⅰ)--A Solid-Liquid Phase Transfer Catalyzed Synthesis of Substituted Cinnamates

虽然含硫碳负离子在有机合成中已有若干应用,但要有效地产生这类碳负离子,通常需用有机锂或氢化钠,这些强碱性试剂对氧和潮气都很敏感,在实际应用方面有不足之处。本文报道在固-液相转移催化条件下,用碳酸钾使α-苯亚磺酰基乙酸甲酯所起的烷基化-消去反应,以合成取代肉桂酸酯类,其反应式如下。

This paper reports a solid-liquid phase transfer catalyzed alkylation elimination of methyl α-phenyl sulfinylacetate and its application for the synthesis of substituted cinnamates. Some improvements have been made in the generation and synthetic application of this α-sulfinyl carbanion by using potassium carbonate as base and Aliquat-336 or TEBA as catalyst. The present procedure provides a convenient and efficient approach to a numoer of α,β-unsaturated esters under mild conditions.