Organocatalytic formal [4 + 2] cycloaddition of o-quinone-methyl derivatives and 2-isocyanatomalonate diesters for the construction of chroman derivatives with adjacent quaternary chiral centers†

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-04-09 DOI:10.1039/D4QO00141A

Tong Xiong, Yi-Zhao Xu, Yao Wang, You-Cai Xiao and Fen-Er Chen

引用次数: 0

Abstract

An asymmetric organocatalytic formal [4 + 2] cycloaddition/annulation cascade of ortho-quinone methides with 2-isocyanatomalonate diesters has been reported. Chromans bearing three contiguous stereogenic centers with a chiral orthoester skeleton were obtained in high yields with excellent enantio- and diastereoselectivities (up to 93% yield, 99% ee and >20 : 1 dr) by using a tertiary amino-urea catalyst.

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有机催化邻醌甲基衍生物和 2-异氰酸基丙二酸二酯的正规 [4 + 2] 环加成，用于构建具有相邻季手性中心的色烷衍生物

据报道，一种不对称的有机催化形式[4 + 2]环加成/嵌合级联反应生成了邻醌甲酯与 2-异氰酸基丙二酸二酯。通过使用叔氨基脲催化剂，高产率地获得了带有手性正酯骨架的三个连续立体中心的色素，并具有极佳的对映和非对映选择性（产率高达 93%，ee 为 99%，dr 为 20 : 1）。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.