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Copper(I)‐Catalyzed Asymmetric Vinylogous Aldol‐Type Reaction of Allylazaarenes
Author(s) -
Wang SiQing,
Liu ZongCi,
Yue WenJun,
Yin Liang
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202013207
Subject(s) - chemistry , aldol reaction , pyrazine , imidazole , nucleophile , pyridine , catalysis , medicinal chemistry , ligand (biochemistry) , double bond , organic chemistry , enantioselective synthesis , nucleophilic addition , biochemistry , receptor
A vinylogous aldol‐type reaction of allylazaarenes and aldehydes is disclosed that affords a series of chiral γ‐hydroxyl‐α,β‐unsaturated azaarenes in moderate to excellent yields with high to excellent regio‐ and enantioselectivities. With ( R , R P )‐TANIAPHOS and ( R , R )‐QUINOXP* as the ligand, the carbon‐carbon double bond in the products is generated in ( E )‐form. With ( R )‐DTBM‐SEGPHOS as the ligand, ( Z )‐form carbon‐carbon double bond is formed in the major product. In this vinylogous reaction, aromatic, α,β‐unsaturated, and aliphatic aldehydes are competent substrates. Moreover, a variety of azaarenes, such as pyrimidine, pyridine, pyrazine, quinoline, quinoxaline, quinazoline, and benzo[d]imidazole are well‐tolerated. At last, the chiral vinylogous product is demonstrated as a suitable Michael acceptor towards CuI‐catalyzed nucleophilic addition with organomagnesium reagents.