Copper(I)-Catalyzed Asymmetric Vinylogous Aldol-Type Reaction of Allylazaarenes
Si-Qing Wang
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
These authors contributed equally to this work.
Search for more papers by this authorZong-Ci Liu
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
These authors contributed equally to this work.
Search for more papers by this authorWen-Jun Yue
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Liang Yin
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
Search for more papers by this authorSi-Qing Wang
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
These authors contributed equally to this work.
Search for more papers by this authorZong-Ci Liu
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
These authors contributed equally to this work.
Search for more papers by this authorWen-Jun Yue
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Prof. Dr. Liang Yin
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032 China
Search for more papers by this authorDedicated to the 70th anniversary of Shanghai Institute of Organic Chemistry (SIOC)
Abstract
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,RP)-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.
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