在本论文中，我们报道了由手性2-异噁唑啉制备(3S,5R)-6-羟基-3,5-O-异亚丙基-3,5-二羟基己酸叔丁酯和相关的顺-1,3-二醇类化合物的工作，这项工作是我们组在手性2-异噁唑啉的不对称合成和应用方面的又一进展。手性1,3-二醇结构在天然产物中是非常普遍的，如(3R)-β-羟基-δ-内酯或其开环化合物顺(3R)-3,5-二羟基戊酸，它是天然物美伐他汀、洛伐他汀等其他相关的他汀类以及合成他汀类药物的常见结构。与传统的片段式连接不同，我们组通过亚烷基氮酸硅醇酯1,3-偶极环加成反应引入了六碳直链，通过实验，探索出了有效的多元醇选择性保护的方法。 由“Cu(II)–双唑啉”催化的氮酸硅醇酯的不对称环加成得到2-异噁唑啉产物，产率为85％，其通过11步反应转化为(3S,5R)-6-羟基-3,5-O-异亚丙基-3,5-二羟基己酸叔丁酯，并对其中稳定的乙基硼酸酯中间体进行了完整的表征。所有新化合物都通过NMR，MS，IR表征，并通过XRD分析确认了(3S,5R)-6-乙酰氧基-3,5-O-异亚丙基-3,5-二羟基己酸叔丁酯的绝对构型，通过HPLC测定了相应的手性异噁唑啉的ee值，并通过旋光仪测定了比旋光度。 本论文还介绍了我的第二部分工作，即螺环吡咯烷酮催化的酮亚胺氢硅烷化反应，这部分工作是在冯立飞师兄合成的配体的基础上，我在其刚性骨架上进行修饰，制备了一系列带有二芳基膦（Ar2P=O）基团或其他新型的基团的化合物，并测试了它们在用HSiCl3还原酮亚胺时的催化性能。我们期望羰基和氧化膦基团作为与HSiCl3配位的路易斯碱性位点起作用，而羧酰胺基团的氢原子作为亚胺氮的键合位点起作用，实验结果表明，具有螺环骨架并且包含二苯氧膦和酰胺结构的化合物作为手性路易斯碱，在催化酮亚胺氢硅烷化反应时取得了较为满意的结果，以99%的收率和86%的ee值得到手性胺。

In this thesis, we report the preparations of t-butyl (3S,5R)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate and related syn-1,3-diol analogues from a chiral 2-isoxazoline. This work is a continuous part of our effort in the asymmetric synthesis and applications of chiral 2-isoxazolines. Chiral 1,3-diol structure is common in a broad spectrum of natural products. (3R)-β-Hydroxy-δ-lactone or its open-ring equivalent (3R)-syn-3,5-dihydroxypentanoic acid, is a common structure in naturally occurring mevastatin (or compactin), lovastatin or closely related statins, and synthetic statins. Construction of the six-carbon linear chain of Kaneka alcohol through a 1,3-dipolar cycloaddition reaction of a silyl nitronate, which differs from the traditional assembly of a four-carbon unit and a two-carbon unit. Through experiments, effective methods for selective protection of polyols were explored. Asymmetric cycloaddition of TIPS nitronate catalyzed by “Cu(II)-bisoxazoline” gave the 2-isoxazoline product in 85% yield, which was converted into t-butyl (3S,5R)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate in 11 steps via a β-hydroxy ketone. A stable ethylboronate intermediate was fully characterized. All new compounds were characterized by NMR, MS, IR, and the absolute configuration of t-butyl (3S,5R)-6-acetoxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate (17) was confimed by single crystal X-ray diffraction analysis. Enantiomeric excess of all chiral isoxazolines were determined by HPLC analysis of the corresponding benzoates and specific rotations were determined. This paper also introduces my second part of the work, Spiro Pyrrolidinone Catalyzed Hydrosilylations of Ketimines. This part of the work is based on the ligand synthesized by Feng Lifei, we prepared a series of new spiro pyrrolidinones bearing a diarylphosphinoyl (Ar2P=O) or other group on the rigid backbone and tested their catalytic performances in ketimine reductions with HSiCl3. We expect the carbonyl group as well as the phosphine oxide group work as Lewis basic sites coordinating with HSiCl3 while the hydrogen atom of the carboxamide group work as a bonding site to the imine nitrogen. The experimental results show that the catalyst with the spiro skeleton and containing the phosphine oxide and amide structure, as a chiral Lewis base, effectively catalyzes the hydrosilylations of ketimines. Satisfactory results were obtained in the reactions, and chiral amines were obtained in up to 99% yield and 86 % ee.