不对称催化Si—H/X—H脱氢偶联构筑硅中心手性
收稿日期: 2023-05-01
修回日期: 2023-06-30
网络出版日期: 2023-07-13
基金资助
国家自然科学基金(22122102); 国家自然科学基金(22101120); 国家自然科学基金(22271134); 广东省催化重点实验室(2020B121201002); 广东省珠江青年拔尖人才(2019QN 01Y628); 及深圳市科技创新委员会(RCJC20221008092723013)
Construction of Silicon-Stereogenic Center via Catalytic Asymmetric Si—H/X—H Dehydrogenative Coupling
Received date: 2023-05-01
Revised date: 2023-06-30
Online published: 2023-07-13
Supported by
National Natural Science Foundation of China(22122102); National Natural Science Foundation of China(22101120); National Natural Science Foundation of China(22271134); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002); Shenzhen Science and Technology Innovation Committee(RCJC20221008092723013); Guangdong Pearl River Talent Program(2019QN01Y628)
硅中心手性有机硅化物因其独特的结构和性质, 在有机合成、功能材料及生物医药等领域展现出特有的价值和应用前景, 受到了化学家们的广泛关注. 近年来, 构筑硅中心手性的方法得到了快速发展, 特别是利用过渡金属催化对前手性硅烷进行去对称化反应. 其中, 以二氢硅烷为底物进行的不对称催化Si—H/X—H脱氢偶联(Si-CADC), 因其具有反应简单高效、原子经济性高、结构多样性好和对映选择性高等优点, 成为了构筑硅中心手性的重要手段和方法. 根据反应类型和产物的不同, 主要从以下三个层次展开综述: (1)不对称脱氢偶联串联策略构筑四取代硅中心手性有机硅烷; (2)分子内Si—H/C—H脱氢偶联构筑环状硅中心手性单氢硅烷; (3)分子间Si—H/X—H脱氢偶联构筑非环状多样化的硅中心手性硅烷.
赵佳怡 , 葛怡聪 , 何川 . 不对称催化Si—H/X—H脱氢偶联构筑硅中心手性[J]. 有机化学, 2023 , 43(10) : 3352 -3366 . DOI: 10.6023/cjoc202305001
Owing to its unique structure and properties, silicon-stereogenic silanes have displayed valuable application prospects in the fields of organic synthesis, functional materials and biomedicine, and have received extensive attention from chemists. In recent years, methods for the construction of silicon-stereogenic center have been rapidly developed, especially the use of transition metal catalysis to conduct the desymmetrization of prochiral silanes. Among them, asymmetric catalytic Si—H/X—H dehydrogenative coupling (Si-CADC) using dihydrosilane as the substrate has become an important approach and key technology for the construction of silicon-stereogenic center, because of its advantages of high efficiency, high atomic economy, good structural diversity and high enantioselectivity. According to the different reaction categorie and products, this review will mainly summarize and discuss in three stages: (1) asymmetric dehydrogenative coupling tandem strategy to construct tetrasubstituted silicon-stereogenic silanes, (2) intramolecular Si—H/C—H dehydrogenative coupling to construct cyclic silicon-stereogenic monohydrosilanes, and (3) intermolecular Si—H/X—H dehydrogenative coupling to construct a variety of ayclic silicon-stereogenic silanes.
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