ChemInform Abstract: Peptide-Catalyzed Stereoselective Conjugate Addition Reactions Generating All-Carbon Quaternary Stereogenic Centers.

ChemInform ◽  
2013 ◽  
Vol 44 (48) ◽  
pp. no-no
Author(s):  
Robert Kastl ◽  
Helma Wennemers
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.

Formation of Quaternary Stereogenic Centers by NHC-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Polyconjugated Cyclic Enones

2012 ◽  
Vol 18 (28) ◽  
pp. 8731-8747 ◽  
Author(s):  
Matthieu Tissot ◽  
Daniele Poggiali ◽  
Hélène Hénon ◽  
Daniel Müller ◽  
Laure Guénée ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Grignard Reagents ◽  
Addition Reactions ◽  
Stereogenic Centers ◽  
Cyclic Enones ◽  
Quaternary Stereogenic Centers
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