手性螺环双氮配体在过渡金属催化中的应用进展
Advances of Chiral Spiro Skeleton-Based Bisnitrogen Ligands in Transition-Metal Catalysis
Received date: 2022-10-12
Revised date: 2022-10-20
Online published: 2022-10-25
手性螺环是配体的优势骨架, 基于螺环结构配体的研究有力地促进了不对称催化领域的发展. 此综述针对基于手性螺环骨架的双氮配体, 按照螺环骨架的类型进行分类, 分别讨论了螺[4.4]壬烷双异噁唑啉(SPRIX)、螺二氢茚双噁唑啉(SpiroBox)、螺二色满双胺(SPANamine)或者双噁唑啉(SPANBox), 以及螺环四氢吡咯-噁唑啉(SPDO)的合成和在过渡金属催化中的应用. 尽管和功能强大、用途广泛的手性螺环膦配体相比, 螺环双氮配体的种类和应用研究还比较有限, 但是这些配体在酸性和(或)氧化反应条件下良好的稳定性以及在催化杂-氢键卡宾插入反应中优异的活性和选择性等特点, 为今后发展新的不对称催化体系提供了重要借鉴.
胡旭东 , 张鑫亮 , 刘文博 . 手性螺环双氮配体在过渡金属催化中的应用进展[J]. 有机化学, 2022 , 42(10) : 3102 -3117 . DOI: 10.6023/cjoc202210010
Chiral spiro skeletons are recognized as a class of “privileged structures” of ligands. Studies toward these spiro ligands have significantly advanced the field of asymmetric catalysis. Bisnitrogen ligands bearing chiral spiro skeletons are reviewed and categorized according to the type of spirocyclic skeletons, including spiro[4.4]nonane-based bis(isoxazoline) ligands (SPRIX), spirobiindane-based bis(oxazoline) ligands (SpiroBox), spirobi(chroman)-based bis(amine) or bis(oxazoline) ligands (SPANamine or SPANBox), and spirocyclic pyrrolidine oxazoline ligands (SPDO). The synthesis and application of these four types of ligands and their applications in transition-metal catalysis are discussed in detail. Compared with the powerful and widely utilized chiral sprio phosphine ligands, the availability and application of spiro bisnitrogen ligands are relatively limited. Nevertheless, their features such as stability under acidic conditions and/or in the presence of an oxidant, superior capability of catalyzing carbene insertion into heteroatom-hydrogen bonds, provide insights and inspirations to the development of novel catalytic systems in asymmetric synthesis.
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