1025217-88-2Relevant articles and documents
Chiral hybrid materials based on pyrrolidine building units to perform asymmetric Michael additions with high stereocontrol
Llopis, Sebastián,García, Teresa,Cantín, ángel,Velty, Alexandra,Díaz, Urbano,Corma, Avelino
, p. 5835 - 5847 (2018)
A new chiral mesoporous hybrid material was synthesized based on pyrrolidine units included in a siliceous framework, HybPyr, and integrated into the organic-inorganic structure, from a specific bis-silylated precursor. A fluoride sol-gel methodology under soft synthesis conditions and in the absence of sophisticated structural directing agents allowed the generation of a mesoporous architecture with a homogeneous distribution of active chiral moieties along the network. The hybrid material was studied by means of different characterization techniques (TGA, NMR and IR spectroscopy, chemical and elemental analyses, TEM, and textural measurements), verifying the stability and integrity of the asymmetric active sites in the solid. The hybrid material, HybPyr, is an excellent asymmetric heterogeneous and recyclable catalyst for enantioselective Michael addition of linear aldehydes to β-nitrostyrene derivatives with high stereocontrol of the reaction products.
Michael addition of carbonyl compounds to nitroolefins under the catalysis of new pyrrolidine-based bifunctional organocatalysts
Castán,Badorrey,Gálvez,López-Ram-De-Víu,Díaz-De-Villegas
, p. 924 - 935 (2018/02/19)
Novel bifunctional pyrrolidine-based organocatalysts for the asymmetric Michael addition of carbonyl compounds to nitroolefins have been synthesised from homoallylamines, which are easily obtained from (R)-glyceraldehyde as a chiral precursor. Under optim
Diphenylprolinol silyl ether-derived thioureas as highly efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes
He, Chunyan,Ren, Xiaochen,Feng, Yingle,Chai, Yonghai,Zhang, Shengyong,Chen, Weiping
supporting information, p. 4036 - 4038 (2015/06/08)
Abstract This Letter described the synthesis of the first diarylprolinol silyl ether-derived bifunctional thiourea organocatalysts. The catalysts were applied to the asymmetric Michael addition of aldehydes to nitroalkenes to give the desired adducts in good yields (up to 99%) with excellent enantioselectivities (up to 99% ee) and excellent diastereoselectivities (up to 99:1). The spatial placement of C-4 substituent is of importance to the reaction activity and stereoselectivity.