A DFT study of the asymmetric (S)-5-(pyrrolidin-2-yl)-1H-tetrazole catalyzed Michael addition of carbonyl compounds to nitroalkenes

2007 ◽  
Vol 18 (2) ◽  
pp. 157-164 ◽  
Author(s):  
Manuel Arnó ◽  
Ramón J. Zaragozá ◽  
Luis R. Domingo
2018 ◽  
Vol 16 (6) ◽  
pp. 924-935 ◽  
Author(s):  
A. Castán ◽  
R. Badorrey ◽  
J. A. Gálvez ◽  
P. López-Ram-de-Víu ◽  
M. D. Díaz-de-Villegas

Novel bifunctional pyrrolidine-based organocatalysts applicable for the asymmetric Michael addition of aldehydes and ketones to nitroolefins have been developed.


2018 ◽  
Vol 14 ◽  
pp. 3018-3024
Author(s):  
Rudolf Knorr ◽  
Barbara Schmidt

Sterically well-shielded against unsolicited Michael addition and polymerization reactions, α-metalated α-(1,1,3,3-tetramethylindan-2-ylidene)acetonitriles added reversibly to three small aldehydes and two bulky ketones at room temperature. Experimental conditions were determined for transfer of the nucleofugal title carbanion unit between different carbonyl compounds. These readily occurring retro-additions via C–C(O) bond fission may also be used to generate different metal derivatives of the nucleofugal anions as equilibrium components. Fluoride-catalyzed, metal-free desilylation admitted carbonyl addition but blocked the retro-addition.


ChemInform ◽  
2003 ◽  
Vol 34 (13) ◽  
Author(s):  
Younes Abrouki ◽  
Mohamed Zahouily ◽  
Ahmed Rayadh ◽  
Bouchaib Bahlaouan ◽  
Said Sebti

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