Kukhtin-Ramirez反应是有机化学中一类重要的极性反转反应.利用三价磷的还原性对α-羰基酮化合物进行极性反转,所生成的Kukhtin-Ramirez活性中间体在诸多转化中都展现出了其作为1,1-偶极子的化学性质.近年来关于该活性中间体的反应研究主要包括:极性X-H键插入反应、还原性加成反应、形式[2+1]环加成反应、形式[4+1]环加成反应、形式[4+2]环加成反应.这些转化为一些重要的多官能团化合成中间体及结构复杂的环状化合物提供了高效简洁的合成方法,凸显了Kukhtin-Ramirez极性反转反应在有机合成中的重要性.
Kukhtin-Ramirez reaction is one type of the important umpolung reactions in organic chemistry. The Kukhtin-Ramirez adducts, which were formed in situ through the umpolung approach by using α-keto carbonyl com- pounds and trivalent phosphorus reducing reagents, have shown the unique reactivity acting as 1,1-dipoles. Focu- sing on the recent development of Kukhtin-Ramirez adducts-initiated transformations, this review mainly summarizes its applications in the following reactions: X--H insertion, reductive addition, formal [2+1] cycloaddition, formal [4+1] cycloaddition, and formal [4+2] cycloaddition. These methodologies based on Kukhtin-Ramirez reaction provide effective synthetic approaches to the construction of densely multi-functionalized building blocks and struc- turally complex cyclic compounds, manifesting the importance of Kukhtin-Ramirez umpolung reaction in organic synthesis.