新的手性二茂铁基吡咯环配体的设计、合成及在不对称催化反应中的应用研究
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摘要
本文以有机合成方法学为目标，从便宜、易得的L-脯氨酸出发，设计、合成了四个新的手性二茂铁基吡咯环单膦配体和十二个新的手性二茂铁基吡咯甲醇配体，研究了这些手性膦配体在催化二乙基锌对亚胺的不对称加成反应和二茂铁基吡咯甲醇配体在催化二乙基锌对醛的不对称加成反应中的应用。
一、新的手性二茂铁基单膦配体的设计、合成及其在催化亚胺不对称加成中的应用
以便宜、易得的L-脯氨酸1为原料，利用简便的合成路线，合成了四个新的手性二茂铁基膦配体5-8，通过核磁共振氢谱、核磁共振碳谱、红外光谱、高分辨质谱等手段对其结构进行了表征，此外还测定了化合物7的晶体结构。研究了这些配体的铜(Ⅱ)配合物在催化二乙基锌对N-对甲基苯磺酰芳醛亚胺的不对称加成反应中的应用，结果表明手性配体5的催化效果最好，在最佳反应条件下，可以达到99％的化学产率和最高86％的ee值，这是目前最好的催化N-对甲
In this thesis, four new ferrocenyl phosphorus-containing compounds and twelve new ferrocenyl pyrrolidino alcohols as chiral ligands were designed and synthesized from readily available natural L-proline. The systematic studies on these phosphorus-containing chiral ligands were carried out for the application in the catalytic asymmetric addition of diethylzinc to imines and on the ferrocenyl pyrrolidino alcohols in the catalytic asymmetric addition of diethylzinc to aldehydes.
1. The synthesis of new chiral ferrocenyl phosphorus-containing ligands and their application in the asymmetric addition of diethylzinc to imines
Starting from L-proline, four new chiral ferrocenyl phosphorus-containing ligands 5-8 were synthesized and characterized by ~1H NMR, ~(13)C NMR, IR and HRMS. The crystal structure of ligand 7 was confirmed by X-ray diffraction. The chiral catalysts composed of compounds 5-8 and Cu(OTf)2 were used to promote the asymmetric
一、新的手性二茂铁基单膦配体的设计、合成及其在催化亚胺不对称加成中的应用
以便宜、易得的L-脯氨酸1为原料，利用简便的合成路线，合成了四个新的手性二茂铁基膦配体5-8，通过核磁共振氢谱、核磁共振碳谱、红外光谱、高分辨质谱等手段对其结构进行了表征，此外还测定了化合物7的晶体结构。研究了这些配体的铜(Ⅱ)配合物在催化二乙基锌对N-对甲基苯磺酰芳醛亚胺的不对称加成反应中的应用，结果表明手性配体5的催化效果最好，在最佳反应条件下，可以达到99％的化学产率和最高86％的ee值，这是目前最好的催化N-对甲
In this thesis, four new ferrocenyl phosphorus-containing compounds and twelve new ferrocenyl pyrrolidino alcohols as chiral ligands were designed and synthesized from readily available natural L-proline. The systematic studies on these phosphorus-containing chiral ligands were carried out for the application in the catalytic asymmetric addition of diethylzinc to imines and on the ferrocenyl pyrrolidino alcohols in the catalytic asymmetric addition of diethylzinc to aldehydes.
1. The synthesis of new chiral ferrocenyl phosphorus-containing ligands and their application in the asymmetric addition of diethylzinc to imines
Starting from L-proline, four new chiral ferrocenyl phosphorus-containing ligands 5-8 were synthesized and characterized by ~1H NMR, ~(13)C NMR, IR and HRMS. The crystal structure of ligand 7 was confirmed by X-ray diffraction. The chiral catalysts composed of compounds 5-8 and Cu(OTf)2 were used to promote the asymmetric
引文
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