Bifunctional primary amine 2-aminobenzimidazole organocatalyst anchored to trans-cyclohexane-1,2-diamine in enantioselective conjugate additions of aldehydes
作者： Talita de A. Fernandes , Pascuala Vizcaíno-Milla , João M.J.M. Ravasco , Aitor Ortega-Martínez , José M. Sansano
DOI: 10.1016/J.TETASY.2015.12.004
关键词:
摘要: Abstract Bifunctional chiral primary amine 8 containing an (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-benzimidazole unit is used as general organocatalyst for the Michael addition of α,α-branched aldehydes to nitroalkenes maleimides. The reactions take place, with 20 mol % catalyst in dichloromethane at rt 15 mol % loading toluene 10 °C maleimides, good yields enantioselectivities. DFT calculations demonstrate bifunctional character this activating aldehyde by enamine formation acceptor double hydrogen bonding.
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Carmen Nájera, Enrique Gómez-Bengoa, Pascuala Vízcaíno-Milla, José Sansano, Béla Fiser, Primary Amine–2-Aminopyrimidine Chiral Organocatalysts for the Enantioselective Conjugate Addition of Branched Aldehydes to Maleimides Synthesis. ,vol. 47, pp. 2199- 2206 ,(2015) , 10.1055/S-0034-1380718
Angel Avila, Rafael Chinchilla, Enrique Gómez-Bengoa, Carmen Nájera, Enantioselective Synthesis of Succinimides by Michael Addition of Aldehydes to Maleimides Organocatalyzed by Chiral Primary Amine‐Guanidines European Journal of Organic Chemistry. ,vol. 2013, pp. 5085- 5092 ,(2013) , 10.1002/EJOC.201300492
Eduardo Gómez-Torres, Diego A. Alonso, Enrique Gómez-Bengoa, Carmen Nájera, Enantioselective Synthesis of Succinimides by Michael Addition of 1,3‐Dicarbonyl Compounds to Maleimides Catalyzed by a Chiral Bis(2‐aminobenzimidazole) Organocatalyst European Journal of Organic Chemistry. ,vol. 2013, pp. 1434- 1440 ,(2013) , 10.1002/EJOC.201201046
Diana Almaşi, Diego A. Alonso, Carmen Nájera, Organocatalytic asymmetric conjugate additions Tetrahedron-asymmetry. ,vol. 18, pp. 299- 365 ,(2007) , 10.1016/J.TETASY.2007.01.023
Pankaj Chauhan, Jasneet Kaur, Swapandeep Singh Chimni, Asymmetric organocatalytic addition reactions of maleimides: a promising approach towards the synthesis of chiral succinimide derivatives. Chemistry-an Asian Journal. ,vol. 8, pp. 328- 346 ,(2013) , 10.1002/ASIA.201200684
Carmen Nájera, Miguel Yus, Chiral benzimidazoles as hydrogen bonding organocatalysts Tetrahedron Letters. ,vol. 56, pp. 2623- 2633 ,(2015) , 10.1016/J.TETLET.2015.03.099
Tomotaka Okino, Yasutaka Hoashi, Yoshiji Takemoto, Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts Journal of the American Chemical Society. ,vol. 125, pp. 12672- 12673 ,(2003) , 10.1021/JA036972Z
Svetlana B. Tsogoeva, Recent Advances in Asymmetric Organocatalytic 1,4-Conjugate Additions European Journal of Organic Chemistry. ,vol. 2007, pp. 1701- 1716 ,(2007) , 10.1002/EJOC.200600653
Mark S. Taylor, Eric N. Jacobsen, Asymmetric catalysis by chiral hydrogen-bond donors. Angewandte Chemie. ,vol. 45, pp. 1520- 1543 ,(2006) , 10.1002/ANIE.200503132
Eduardo Gómez-Torres, Diego A. Alonso, Enrique Gómez-Bengoa, Carmen Nájera, Conjugate addition of 1,3-dicarbonyl compounds to maleimides using a chiral C2-symmetric bis(2-aminobenzimidazole) as recyclable organocatalyst. Organic Letters. ,vol. 13, pp. 6106- 6109 ,(2011) , 10.1021/OL202599H