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Phosphine-catalyzed [4 + 2] cyclization of para-quinone methide derivatives with allenes. 2019

Fu-Ru Yuan, and Fei Jiang, and Ke-Wei Chen, and Guang-Jian Mei, and Qiong Wu, and Feng Shi
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, China. fshi@jsnu.edu.cn.

The first [4 + 2] cyclization of para-quinone methide (p-QM) derivatives with allenes has been established via phosphine catalysis, which afforded a series of chroman derivatives in high yields (up to 97%) and excellent (E/Z)-selectivities (all >95 : 5 E/Z). This reaction will not only enrich the research contents of cyclization reactions involving p-QM derivatives, but also provide a good example of the application of allenes and phosphine catalysis in cyclization reactions. In addition, this approach also offers a useful method for the construction of chroman scaffolds.

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