硅氨基镧化合物催化合成磷酸烯醇酯
收稿日期: 2023-06-15
修回日期: 2023-07-13
网络出版日期: 2023-07-27
基金资助
江苏省高等学校自然科学研究(18KJA150007)
Lanthanum Silylamide-Catalyzed Synthesis of Enol Phosphates
Received date: 2023-06-15
Revised date: 2023-07-13
Online published: 2023-07-27
Supported by
Natural Science Foundation of the Jiangsu Higher Education Institutions(18KJA150007)
磷酸烯醇酯有重要的应用价值, 发展催化的选择性合成磷酸烯醇酯的方法很有意义. 以硅氨基镧化合物[(Me3Si)2N]3La(μ-Cl)Li(THF)3催化4-氧代-4-芳基-2-丁烯酸酯和亚磷酸酯的反应, 合成了一系列单一cis-构型的磷酸烯醇酯. 对机理的研究表明, 反应经历了较为少见的[1,4]-phospha-Brook重排. 反应的催化剂易得, 立体选择性好, 为合成cis-构型的磷酸烯醇酯提供了一种有效的新途径.
关键词： 磷酸烯醇酯; 硅氨基稀土化合物; 催化; phospha-Brook重排; 立体选择性
潘康 , 徐凡 . 硅氨基镧化合物催化合成磷酸烯醇酯[J]. 有机化学, 2023 , 43(12) : 4261 -4267 . DOI: 10.6023/cjoc202306012
Enol phosphate has important applicative value in many fields. The development of a catalytic and selective method for the synthesis of enol phosphate is of great significance. The reaction of 4-oxo-4-arylbut-2-enoate and diethyl phosphite catalyzed by lanthanum silylamide [(Me3Si)2N]3La(μ-Cl)Li(THF)3 is developed, which provides a series of enol phosphates in cis-configuration. Research on the mechanism indicates that the reaction undergoes a relatively rare [1,4]-phospha-Brook rearrangement. The reaction has advantages of ready availability of catalyst and high selectivity for alkenyl configuration, providing an efficient method for the synthesis of enol phosphates.
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