Stereodivergent 1,5-Conjugate Addition with Iminoesters via Pd/Cu Dual Catalysis

Zi-Jiang Yang; Zhi-Tao He

doi:10.1055/a-2230-4562

Synthesis, Table of Contents

Synthesis 2024; 56(22): 3412-3420
DOI: 10.1055/a-2230-4562

paper

Dual Catalysis

Stereodivergent 1,5-Conjugate Addition with Iminoesters via Pd/Cu Dual Catalysis

Zi-Jiang Yang

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, P. R. of China

,

Zhi-Tao He ∗

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, P. R. of China

^cSchool of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, P. R. of China

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Abstract

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Abstract

The first stereodivergent umpolung 1,5-conjugate addition reaction via synergistic Pd/Cu catalysts is reported. By dictating the absolute configuration of each chiral ligand ligated to corresponding metals, all four stereoisomers of the products are easily achieved. A series of amino acid moieties are introduced to the γ-position of the conjugated esters in high yields with excellent diastereoselectivities and enantioselectivities. The downstream transformations highlight the synthetic value of the method.

Key words

stereodivergent - 1,5-conjugate addition - palladium - copper - synergistic catalysis

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