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有机小分子催化是有机化学研究的热点和前沿领域,是与传统的金属催化、酶催化并列的三大催化方法之一,在手性合成领域有着广泛的应用前景。TADDOL作为一种重要的有机小分子催化剂,可活化醛、酮、亚胺等化合物,能够高效催化不对称的Diels-Alder等反应。主要从天然的酒石酸出发,经过酯化反应,双羟基保护,格氏反应,重结晶提纯,最终合成了三种手性TADDOL,并对各步反应产物进行了结构表征,证明了合成路线设计的合理性。
Organic small molecule catalysis is a hot and frontier field of organic chemistry research. It is one of the three catalysis methods which are parallel with traditional metal catalysis and enzyme catalysis. It has a wide range of application prospects in the field of chiral synthesis. As an important organic small molecule catalyst, TADDOL can activate aldehydes, ketones, imines and other compounds and can efficiently catalyze the asymmetric Diels-Alder reaction. Starting from natural tartaric acid, three kinds of chiral TADDOLs were finally synthesized through esterification reaction, double hydroxyl protection, Grignard reaction and recrystallization. The structures of the reaction products were characterized and proved that the synthetic route design rationality.