科研之友
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摘要
alpha-Chiral azides are widely used in the fields of synthetic chemistry, medicinal chemistry and life science. Owing to alpha-chiral azides can be used for the diverse synthesis of alpha-chiral amine derivatives and nitrogen-containing heterocycles, and its azido group is also a pharmacophore, the efficient synthesis of alpha-chiral azides is highly important for drug discovery and development. Along with the incorporation of chiral quaternary carbon that can increase the three-dimensional stereospecificity of molecules has become an effective strategy to improve the bioactivity and druggability in drug design and development, the development of catalytic asymmetric synthetic methods toward alpha-chiral tertiary azides featuring aza-quaternary carbon center is highly desirable to facilitate drug research. However, due to the adverse steric effects caused by the structure of azido group that is close to a straight line, and the challenge of distinguishing the substituents with less difference to construct the aza-quaternary carbon stereocenter, the catalytic asymmetric protocols with high enantioselectivity are relatively scarce. This review aims to summarize the advances of the past five years according to the following two strategies: asymmetric functionalizations of C-N-3 bond containing compounds and asymmetric azidations involving C-N-3 bond forming, as well as discusses the possible reaction mechanism, the advantages and disadvantages of different reactions, which would provide some references and inspiration for researchers engaged in organic synthesis and medicinal chemistry.
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单位中国科学院; 海南师范大学
