132482-05-4Relevant articles and documents
LIGAND EFFECTS IN ENANTIOFACE DIFFERENTIATING 1,4 ADDITION TO 1,3 DIPHENYL-2 PROPEN-1 ONE
Leyendecker, Francois,Jesser, Francis,Laucher, Dominique
, p. 3513 - 3516 (1983)
The extent of enantiomeric excess in the β-methylation of chalcone by chiral cuprates is shown to depend strongly on small structural modifications of the ligands, all of which are derived from the basic carbon framework of L-prolinol.Enantiomeric excesses up to 88percent have been realised.
Diastereoselective synthesis of (-)-1-methyl-(3S,4R)-3,4-bis((2S)-N- (tert-butyloxycarbonyl)pyrrolidin-2-yl)-2-pyrrolidinone by an asymmetric Michael reaction
Mahboobi, Siavosh,Popp, Alfred,Burgemeister, Thomas,Schollmeyer, Dieter
, p. 2369 - 2376 (1998)
Beginning with enantiomerically pure L-proline, (-)-1-methyl-(3S,4R)- 3,4-bis((2S)-N-(tert-butyloxycarbonyl)pyrrolidin-2-yl)-2-pyrrolidinone was prepared in diastereomerically pure form. Taking advantage of the chiral induction of the L-proline derivatives, the intermolecular Michael reaction, used to build the pyrrolidinone ring, was carried out stereoselectively.
Iminium ion-enamine cascade cyclizations: Facile access to structurally diverse azacyclic compounds and natural products
Hanessian, Stephen,Chattopadhyay, Amit Kumar
supporting information, p. 232 - 235 (2014/01/23)
A one-pot, mild, two-component iminium ion-enamine cascade reaction to construct structurally diverse azacyclic frameworks from l-proline and l-pipecolic acid, and its application to indolizidine and quinolizidine alkaloids and azasteroids, is reported.
A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes
Liu, Chang-Lu,Wei, Chang-Yong,Wang, Shi-Wen,Peng, Yun-Gui
experimental part, p. 921 - 928 (2012/06/17)
Homoprolinol analogs, a class of optically active γ-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ-amino alcohols with those by the β-amino alcohols based on pyrrolidine architecture reported in the literature references, we have observed that the γ-amino alcohols are superior to the corresponding β-amino alcohols when the nitrogen and the oxygen are unsubstituted. Among the homoprolinols we tested, 2b gave the best results (45-88% yields, 44-81% ee) in the addition reactions. To the best of our knowledge, 2b has been noticed as one of the most efficient γ-amino alcohol catalysts based on pyrrolidine framework.