Organocatalyzed Enantioselective Synthesis of Nitroalkanes Bearing All-Carbon Quaternary Stereogenic Centers through Conjugate Addition of Acetone Cyanohydrin

Synlett ◽  
2008 ◽  
Vol 2008 (12) ◽  
pp. 1857-1861 ◽  
Author(s):  
Mariafrancesca Fochi ◽  
Alfredo Ricci ◽  
Luca Bernardi ◽  
Francesco Fini
Keyword(s):  
Conjugate Addition ◽  
Enantioselective Synthesis ◽  
Acetone Cyanohydrin ◽  
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.

scholarly journals Enantioselective synthesis of gem-diarylalkanes by transition metal-catalyzed asymmetric arylations (TMCAAr)

2018 ◽  
Vol 9 (3) ◽  
pp. 546-559 ◽  
Author(s):  
Tao Jia ◽  
Peng Cao ◽  
Jian Liao
Keyword(s):  
Transition Metal ◽  
Enantioselective Synthesis ◽  
Transfer Reactions ◽  
Stereogenic Centers ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Quaternary Stereogenic Centers ◽  
Aryl Transfer

To date, enantiomerically enriched molecules containing gem(1,1)-diaryl containing tertiary or quaternary stereogenic centers have been readily accessed by transition metal-catalyzed enantioselective or stereoconvergent aryl transfer reactions.

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