Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides
Si-Jia Liu,
Man-Su Tu,
Kai-Yue Liu,
Jia-Yi Chen,
Shao-Fei Ni,
Yu-Chen Zhang,
Feng Shi
Affiliations
Si-Jia Liu
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, China
Man-Su Tu
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, China
Kai-Yue Liu
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, China
Jia-Yi Chen
Department of Chemistry, Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou 515063, China
Shao-Fei Ni
Department of Chemistry, Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou 515063, China
Yu-Chen Zhang
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, China
Feng Shi
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, China
Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with ortho-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.
