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

Author:

Sayed Mostafa,Han Zhi-Yong1,Shi Zhipeng1,Fan Tao1,Shen Hong-Cheng1

Affiliation:

1. Department of Chemistry, University of Science and Technology of China

Abstract

AbstractA 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.

Funder

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

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