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Switchable Mono‐ and Dipropargylation of Amino Alcohols: A Unique Property of the Iodide Anion in Controlling Ring‐Opening Alkynylation
Author(s) -
Feng Huangdi,
Wang Fang,
Cao Leilei,
Van der Eycken Erik V.,
Yin Xiaoying
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100634
Subject(s) - chemistry , annulation , oxazolidine , iodide , copper , propargyl , ring (chemistry) , combinatorial chemistry , alcohol , vicinal , catalysis , alkynylation , selectivity , organic chemistry , propargyl alcohol
The application of multicomponent reactions has been recognized as the most versatile strategy to achieve molecular diversity in organic synthesis. The reaction pathway and selectivity control of multicomponent reactions are associated with the effectiveness, the economy, and cleanliness of the process. Herein, a copper‐catalyzed switchable process for the selective synthesis of N ‐propargyl oxazolidines and N , N ‐dipropargyl vicinal amino alcohols, by propargylation of amino alcohols, is disclosed. Mechanistic studies support a sequential process involving a copper‐catalyzed annulation/A 3 ‐coupling of amino alcohol, and copper‐catalyzed ring‐opening alkynylation of the oxazolidine intermediate. Notably, the iodide anion would not affect the generation of oxazolidines, but it could shut down the cascade procedure of the alkynylation of these oxazolidines.