ChemInform Abstract: Formation of Quaternary Stereogenic Centers by Copper-Catalyzed Asymmetric Conjugate Addition Reactions of Alkenylaluminums to Trisubstituted Enones.

ChemInform ◽  
2014 ◽  
Vol 45 (13) ◽  
pp. no-no
Author(s):  
Daniel Mueller ◽  
Alexandre Alexakis
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Stereogenic Centers ◽  
Quaternary Stereogenic Centers

Asymmetric Conjugate Addition of α-Cyanoketones to Benzoyl Acrylonitrile Derivatives Using a Diaminomethylenemalononitrile Organocatalyst

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3874-3880 ◽  
Author(s):  
Tsuyoshi Miura ◽  
Hiroshi Akutsu ◽  
Kosuke Nakashima ◽  
Yuta Kanetsuna ◽  
Masahiro Kawada ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Conjugate Addition ◽  
Significant Loss ◽  
Addition Reactions ◽  
Dicarbonyl Compounds ◽  
Stereogenic Centers ◽  
Synthetic Intermediates ◽  
Quaternary Stereogenic Centers

AbstractA diaminomethylenemalononitrile (DMM) organocatalyst was used to efficiently promote asymmetric conjugate addition of various α-cyanoketones to benzoyl acrylonitrile derivatives. The corresponding 1,5-dicarbonyl compounds containing vicinal tertiary and quaternary stereogenic centers are versatile synthetic intermediates and were obtained in good yields and with excellent enantioselectivities (up to 96% ee). The present study describes the first successful examples of asymmetric conjugate addition reactions of α-cyanoketones with benzoyl acrylonitriles. In addition, the DMM organocatalyst can be recovered and reused up to five times without significant loss of either catalytic activity or enantioselectivity.

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