Asymmetric Supramolecular Catalysis: A Bio-Inspired Tool for the High Asymmetric Induction in the Enamine-Based Michael Reactions

2012 ◽  
Vol 18 (26) ◽  
pp. 8008-8012 ◽  
Author(s):  
Dhevalapally B. Ramachary ◽  
Rajasekar Sakthidevi ◽  
Kodambahalli S. Shruthi
Keyword(s):  
Asymmetric Induction ◽  
Supramolecular Catalysis ◽  
Michael Reactions

Asymmetric induction in domino Heck-aza-Michael reactions

2012 ◽  
Vol 53 (12) ◽  
pp. 1468-1471 ◽  
Author(s):  
Daniel L. Priebbenow ◽  
Scott G. Stewart ◽  
Frederick M. Pfeffer
Keyword(s):  
Asymmetric Induction ◽  
Michael Reactions

Enantioselective Michael Addition of Malonates to Enones

2020 ◽  
Vol 24 (7) ◽  
pp. 746-773
Author(s):  
Péter Bakó ◽  
Tamás Nemcsok ◽  
Zsolt Rapi ◽  
György Keglevich
Keyword(s):  
Michael Addition ◽  
Activity Relationship ◽  
Chalcone Derivatives ◽  
Michael Additions ◽  
Michael Reactions ◽  
Structure Activity ◽  
Cyclic Enones ◽  
Michael Acceptors ◽  
Relationship Of ◽  
Enantioselective Catalysts

: Many catalysts were tested in asymmetric Michael additions in order to synthesize enantioenriched products. One of the most common reaction types among the Michael reactions is the conjugated addition of malonates to enones making it possible to investigate the structure–activity relationship of the catalysts. The most commonly used Michael acceptors are chalcone, substituted chalcones, chalcone derivatives, cyclic enones, while typical donors may be dimethyl, diethyl, dipropyl, diisopropyl, dibutyl, di-tert-butyl and dibenzyl malonates. This review summarizes the most important enantioselective catalysts applied in these types of reactions.

P-Chiral 2-{1'-[Butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazoles: A Second Chirality Center in Catalytic System

2005 ◽  
Vol 70 (3) ◽  
pp. 361-369 ◽  
Author(s):  
Dušan Drahoňovský ◽  
Petr Štěpnička ◽  
Dalimil Dvořák
Keyword(s):  
Catalytic System ◽  
Asymmetric Induction ◽  
Dimethyl Malonate ◽  
Enantiomerically Pure

P-Chiral (S,RP)-2-{1'-[butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazole (6) and (S,SP)-2-{1'-[butyl(phenyl)phosphanyl]ferrocen-1-yl}-4-isopropyl-4,5-dihydrooxazole (7) were prepared by the procedure developed by Jugé, starting from enantiomerically pure (-)- or (+)-ephedrine and dichloro(phenyl)phosphine. Compounds 6 and 7 were examined for asymmetric induction in the Pd-catalyzed reaction of rac-1,3-diphenylallyl acetate with dimethyl malonate. The best results were obtained with 7 (98% ee), while 6 gave 82% ee.

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