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

doi:10.6023/cjoc201301080

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (04): 848-853.DOI: 10.6023/cjoc201301080 Previous Articles Next Articles

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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

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).

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

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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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