An enantioselective four-component reaction via assembling two reaction intermediates

Sifan Yu, Wenju Chang, Ruyu Hua, Xiaoting Jie, Mengchu Zhang, Wenxuan Zhao, Jinzhou Chen, Dan Zhang, Huang Qiu (), Yong Liang () and Wenhao Hu ()
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Sifan Yu: Sun Yat-sen University
Wenju Chang: Nanjing University
Ruyu Hua: Sun Yat-sen University
Xiaoting Jie: Sun Yat-sen University
Mengchu Zhang: Sun Yat-sen University
Wenxuan Zhao: Nanjing University
Jinzhou Chen: Sun Yat-sen University
Dan Zhang: Sun Yat-sen University
Huang Qiu: Sun Yat-sen University
Yong Liang: Nanjing University
Wenhao Hu: Sun Yat-sen University

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract A reaction intermediate is a key molecular entity that has been used in explaining how starting materials converts into the final products in the reaction, and it is usually unstable, highly reactive, and short-lived. Extensive efforts have been devoted in identifying and characterizing such species via advanced physico-chemical analytical techniques. As an appealing alternative, trapping experiments are powerful tools in this field. This trapping strategy opens an opportunity to discover multicomponent reactions. In this work, we report various highly diastereoselective and enantioselective four-component reactions (containing alcohols, diazoesters, enamines/indoles and aldehydes) which involve the coupling of in situ generated intermediates (iminium and enol). The reaction conditions presented herein to produce over 100 examples of four-component reaction products proceed under mild reaction conditions and show high functional group tolerance to a broad range of substrates. Based on experimental and computational analyses, a plausible mechanism of this multicomponent reaction is proposed.

Date: 2022
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DOI: 10.1038/s41467-022-34913-2

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