Stereoselective Synthesis of 3,4-Dihydrobenzofuro[3,2-b]pyridin-2(1H)-ones Enabled by Pd/Chiral Isothiourea Relay Catalysis

Mostafa Sayed; Zhipeng Shi; Tao Fan; Hong-Cheng Shen; Zhi-Yong Han

doi:10.1055/s-0043-1763679

Synthesis, Table of Contents

Synthesis 2024; 56(09): 1381-1392
DOI: 10.1055/s-0043-1763679

paper

Stereoselective Synthesis of 3,4-Dihydrobenzofuro[3,2-b]pyridin-2(1H)-ones Enabled by Pd/Chiral Isothiourea Relay Catalysis

Mostafa Sayed∗

^aDepartment of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China

^bChemistry Department, Faculty of Science, New Valley University, El-Kharja 72511, Egypt

,

Zhipeng Shi

^aDepartment of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China

,

Tao Fan

^aDepartment of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China

,

Hong-Cheng Shen

^aDepartment of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China

,

Zhi-Yong Han∗

^aDepartment of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China

› Author Affiliations

Abstract

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Abstract

A highly enantioselective [4+2] cyclization of azadienes with ketene in situ generated from Pd-catalyzed carbonylation of benzyl bromides, is established through Pd/chiral isothiourea relay catalysis. The key in this transformation is the formation of a C1-ammonium enolate from the in situ generated ketene and a chiral isothiourea catalyst, which subsequently undergoes a formal [4+2] reaction, leading to 3,4-dihydrobenzofuro[3,2-b]pyridine derivatives in high yields and excellent levels of stereoselectivity.

Key words

relay catalysis - C1-ammonium enolate - chiral isothiourea - azadiene - asymmetric catalysis

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References

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