Pd/Mengphos-Catalyzed High-Order [4+4] Cycloaddition for Efficient Synthesis of Oxazocines

Yinggao Meng; Mengya Xu; Yingying Xia; Huiwen Mei; Xiucheng Bi; Xin Zhou; Xin Han

doi:10.1055/a-2435-5589

Synthesis, Table of Contents

Synthesis 2024; 56(24): 3870-3878
DOI: 10.1055/a-2435-5589

paper

Pd/Mengphos-Catalyzed High-Order [4+4] Cycloaddition for Efficient Synthesis of Oxazocines

Authors

Yinggao Meng∗

^aShiyan Key Laboratory of Biological Resources and Eco-environmental Protection, College of Chemical and Environmental Engineering, Hanjiang Normal University, Shiyan, Hubei 442000, P. R. of China
Mengya Xu

^bCollege of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. of China
Yingying Xia

^aShiyan Key Laboratory of Biological Resources and Eco-environmental Protection, College of Chemical and Environmental Engineering, Hanjiang Normal University, Shiyan, Hubei 442000, P. R. of China
Huiwen Mei

^aShiyan Key Laboratory of Biological Resources and Eco-environmental Protection, College of Chemical and Environmental Engineering, Hanjiang Normal University, Shiyan, Hubei 442000, P. R. of China
Xiucheng Bi

^aShiyan Key Laboratory of Biological Resources and Eco-environmental Protection, College of Chemical and Environmental Engineering, Hanjiang Normal University, Shiyan, Hubei 442000, P. R. of China
Xin Zhou

^aShiyan Key Laboratory of Biological Resources and Eco-environmental Protection, College of Chemical and Environmental Engineering, Hanjiang Normal University, Shiyan, Hubei 442000, P. R. of China
Xin Han∗

^aShiyan Key Laboratory of Biological Resources and Eco-environmental Protection, College of Chemical and Environmental Engineering, Hanjiang Normal University, Shiyan, Hubei 442000, P. R. of China

Abstract

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Abstract

The development of new catalytic systems that enable regio- and chemoselective construction of diversely functionalized oxazocines is an important topic in organic synthesis and pharmacochemistry. Herein, a novel Pd/Mengphos complex was designed and applied in a palladium-catalyzed high-order [4+4] cycloaddition of 2-substituted allylic carbonates to α,β-unsaturated imines, allowing facile access to versatile oxazocines in good yields with excellent b/l and Z/E selectivities (up to 92% yield and complete b/l and Z/E selectivities). The reaction exhibited a broad substrate scope, mild reaction conditions, and good functional group compatibility. In addition, an asymmetric version has also been tested, affording the desired oxazocines in moderate to good enantioselectivity.

Key words

palladium catalysis - Mengphos - [4+4] cycloaddition - α,β-unsaturated imines - allyl carbonates - oxazocines

Full Text

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Supplementary Material

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