TY - JOUR
T1 - An enantioselective four-component reaction via assembling two reaction intermediates
AU - YU, Sifan
AU - Chang, Wenju
AU - Hua, Ruyu
AU - Jie, Xiaoting
AU - Zhang, Mengchu
AU - Zhao, Wenxuan
AU - Chen, Jinzhou
AU - Zhang, Dan
AU - Qiu, Huang
AU - Liang, Yong
AU - Hu, Wenhao
N1 - W.H. and H.Q. acknowledge the financial support from Guangdong Innovative and Entrepreneurial Research Team Program (No. 2016ZT06Y337). W.H. and H.Q. acknowledge the National Natural Science Foundation of China (NO. 92056201). H.Q. acknowledges support from NSFC grant 21801255. Y.L. acknowledges support from the Fundamental Research Funds for the Central Universities (020514380253, 020514380277), the Natural Science Foundation of Jiangsu Province (BK20211555), and the Jiangsu Innovation & Entrepreneurship Talents Plan.
Publisher Copyright:
© The Author(s) 2022
PY - 2022/11/18
Y1 - 2022/11/18
N2 - 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.
AB - 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.
UR - https://www.nature.com/articles/s41467-022-34913-2
U2 - 10.1038/s41467-022-34913-2
DO - 10.1038/s41467-022-34913-2
M3 - Journal article
SN - 2041-1723
VL - 13
JO - Nature Communications
JF - Nature Communications
M1 - 7088
ER -
