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

Author:

He Zhi-Tao123ORCID,Yang Zi-Jiang12

Affiliation:

1. College of Chemistry and Materials Science, Sichuan Normal University

2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences

3. School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences

Abstract

AbstractThe 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.

Funder

Science and Technology Commission of Shanghai Municipality

Natural Science Foundation of Ningbo Municipality

National Natural Science Foundation of China

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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