【摘 要】
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Water is the most ubiquitous solvent used in bioorganic chemistry,generating complicated molecules with high efficiencies.Considering the unique reactivity and selectivity with water as the solvent in
【机 构】
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Department of Chemistry,Huaibei Normal University,Huaibei,235000
【出 处】
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中国化学会第十六届全国有机合成化学学术研讨会
论文部分内容阅读
Water is the most ubiquitous solvent used in bioorganic chemistry,generating complicated molecules with high efficiencies.Considering the unique reactivity and selectivity with water as the solvent in biological systems,organic chemists are continually searching for chemical transformations in aqueous media.1 However,in vitro organic synthesis remains limited due to the poor solubility of organics in water.In the pioneering work of Breslow,Sharpless,2 the role of water in accelerating the rate of the reaction was disclosed,and the concept of the “On Water” reaction was introduced into organic chemistry.In our work,the unique reactivity of water in the direct catalytic vinylogous aldol reaction of silyl glyoxylates is reported(Fig.1).With the hydrogen bonding networks from water,the unfavourable homogeneous reactions in organic solvents were severely suppressed,and the "On Water" relay chemistry for the vinylogous aldol reaction was realized in heterogeneous conditions(water as solvent),providing the desired products with all-carbon quaternary stereocenters in high yields.Moreover,the new insights on the role of water in biological systems were demonstrated with this strategy.
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