L-脯氨酸衍生的手性N,P-配体的合成及其在不对称1,3-偶极环加成反应中的应用

doi:10.6023/cjoc201301080

有机化学 ›› 2013, Vol. 33 ›› Issue (04): 848-853.DOI: 10.6023/cjoc201301080 上一篇下一篇

研究论文

L-脯氨酸衍生的手性N,P-配体的合成及其在不对称1,3-偶极环加成反应中的应用

陈虹, 陈谦

哈尔滨工业大学基础与交叉科学研究院城市水资源与水环境国家重点实验室哈尔滨 150080

收稿日期:2013-01-31 修回日期:2013-02-26 发布日期:2013-03-01
通讯作者: 陈谦 E-mail:chenqian@hit.edu.cn
基金资助:
国家自然科学基金(No. 20902015)和中央高校基础研究基金(No. 2010055)资助项目.

Synthesis of Chirl N,P-ligands Derived from L-Proline and Its Application to 1,3-Dipolar Cycloaddition

Chen Hong, Chen Qian

State Key Laboratory of Urban Water Resource and Environment & Academy of Fundamental and Interdisciplinary Science, Harbin Institute of Technology, Harbin 150080

Received:2013-01-31 Revised:2013-02-26 Published:2013-03-01
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20902015) and the Fundamental Research Funds for the Central Universities (No. 2010055).

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摘要/Abstract

从L-脯氨酸衍生而来的酰胺膦类化合物1, 经脱去保护基得到的氨基膦2, 用正丁基锂处理后, 用2-甲氧基吡啶类化合物捕获, 得到一类吡啶型的手性N,P-配体4; 氨基醇与碳酸二乙酯生成的噁唑啉酮6, 与四氟硼酸三乙氧基鎓盐反应制得的乙氧基噁唑啉7直接与氨基膦2反应, 合成了噁唑啉型手性N,P-配体8. 将两类手性N,P-配体应用于Ag(I)催化的1,3-偶极环加成反应, 通过对反应条件进行优化, 发现手性N,P-配体与AgOTf所形成的催化剂能很好地催化1,3-偶极环加成反应, 最高可以以93%的收率获得环加成产物, ee值最高可以达到15%.

关键词: L-脯氨酸, 手性N,P-配体, 1,3-偶极环加成

Aminophosphine 2 was obtained by deprotection of amidophosphine 1, which was derived from L-proline. Deprotonation of aminophosphine 2 with n-BuLi, and then being captured by 2-MeO-pyridine gave chiral pyridyl N,P-ligands 4. Reaction of aminoalcohol and diethyl carbonate afforded oxazolidione 6, which was converted to compounds 7 by the reaction with triethyloxonium tetrafluoroborate. Chiral N,P-ligands 8 were obtained by the reaction of compounds 7 with aminophosphine 2. Two kinds of chiral N,P-ligands shown excellent catalytic activity in Ag(I) catalytic asymmetric 1,3-dipolar cycloaddition, and up to 93% yield and 15% ee were obtained.

Key words: L-proline, chiral N,P-ligands, asymmetric 1,3-dipolar cycloaddition

引用此文

陈虹, 陈谦. L-脯氨酸衍生的手性N,P-配体的合成及其在不对称1,3-偶极环加成反应中的应用[J]. 有机化学, 2013, 33(04): 848-853.

Chen Hong, Chen Qian. Synthesis of Chirl N,P-ligands Derived from L-Proline and Its Application to 1,3-Dipolar Cycloaddition[J]. Chin. J. Org. Chem., 2013, 33(04): 848-853.

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L-脯氨酸衍生的手性N,P-配体的合成及其在不对称1,3-偶极环加成反应中的应用

Synthesis of Chirl N,P-ligands Derived from L-Proline and Its Application to 1,3-Dipolar Cycloaddition

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