McVeigh Matthew S, Sorrentino Jacob P, Hands Allison T, Garg Neil K
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
J Am Chem Soc. 2024 Jun 5;146(22):15420-15427. doi: 10.1021/jacs.4c03369. Epub 2024 May 20.
We report the strain-induced [2 + 2] cycloadditions of cyclic allenes for the assembly of highly substituted cyclobutanes. By judicious choice of trapping agent, complex scaffolds bearing heteroatoms, fused rings, contiguous stereocenters, spirocycles, and quaternary centers are ultimately accessible. Moreover, we show that the resulting cycloadducts can undergo thermal isomerization. This study provides an alternative strategy to photochemical [2 + 2] cycloadditions for accessing highly functionalized cyclobutanes, while validating the use of underexplored strained intermediates for the assembly of complex architectures.
我们报道了环丙二烯的应变诱导[2 + 2]环加成反应，用于构建高度取代的环丁烷。通过明智地选择捕获剂，最终可以获得带有杂原子、稠环、相邻立体中心、螺环和季碳中心的复杂支架。此外，我们表明所得的环加成产物可发生热异构化。这项研究为光化学[2 + 2]环加成反应提供了一种替代策略，用于获得高度官能化的环丁烷，同时验证了利用未充分探索的应变中间体来构建复杂结构的方法。
