通过邻羟基苯基膦和醛的缩合反应合成苯并氧杂磷杂环戊烯  

Synthesis of Dihydrobenzooxaphospholes via Cyclocondensation of 2-Phosphinylphenol and Aldehydes

作　　者：朱雪莉 杨绍丽 郏彩霞 李静[2] 段征[1] Zhu Xueli;Yang Shaoli;Jia Caixia;Li Jing;Duan Zheng(College of Chemistry,Green Catalysis Center,International Phosphorus Laboratory,International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province,Zhengzhou University,Zhengzhou 450001;School of Chemistry,Xi'an Jiaotong University,Xi'an 710049)

机构地区：[1]郑州大学化学学院,绿色催化研究中心国际磷化学实验室,河南省有机磷功能分子国际联合实验室,郑州450001 [2]西安交通大学化学学院,西安710049

出　　处：《有机化学》2022年第7期2201-2213,共13页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.22171245,21672193)资助项目.

摘　　要：报道了一种利用简单易得的底物,通过酸促进的缩合环化反应来合成2,3-二氢苯并[d][1,3]氧杂磷杂环戊烯类化合物的新路线.该反应操作简便,通过普通硅胶色谱即可实现反应中产生的非对映异构体的分离,可应用于克级规模合成.当改用联萘酚磷酸酯[(±)-BINOL-phosphoricacids]为缩合反应促进剂时,可以实现高非对映立体选择性的构筑苯并氧杂磷杂环戊烯类化合物.A facile method to synthesize dihydrobenzooxaphospholes was developed from a p-toluenesulfonic acid(p-TSA)-promoted intermolecular cyclocondensation of the readily available 2-phosphinylphenol and aromatic aldehydes.The desired products were obtained as a mixture of stereoisomers.Interestingly,the diastereoisomers could be separated easily by flash column chromatography.The gram-scale and diastereoselective syntheses were also successfully performed.

关 键 词：有机磷 苯并氧杂磷杂环戊烯 缩合反应 非对映选择性 

分 类 号：O626[理学—有机化学]