929030-93-3Relevant academic research and scientific papers
Acetals: A new organocatalysis chemotype for one-pot enantioselective α-amination
Msutu, Ath'Enkosi,Hunter, Roger
supporting information, p. 2295 - 2298 (2014/04/17)
Conditions are described for one-pot Br?nsted acid and organocatalysed enantioselective α-amination of acetals and associated functionalities. Of the organocatalysts screened, proline tetrazole gave the highest ee, while aqueous monochloroacetic acid proved to be the best Br?nsted acid activator regarding minimizing racemization and maximizing product yield. The reaction opens up the way for using masked carbonyl functionalities in organocatalysis.
Construction of quaternary stereocenters: Asymmetric α-amination of branched aldehydes catalyzed by monoimide substituted cyclohexane-1,2-Diamines
Fu, Ji-Ya,Wang, Qi-Lin,Peng, Lin,Gui, Yong-Yuan,Xu, Xiao-Ying,Wang, Li-Xin
, p. 668 - 672 (2013/09/24)
A highly efficient enantioselective α-amination of branched aldehydes catalyzed by chiral imide monosubstituted 1,2-diamine derivatives was reported to afford the quaternary stereogenic centers in excellent yields (up to 99%) and enantioselectivities (up to 97% ee). Chirality 25:668-672, 2013. 2013 Wiley Periodicals, Inc α-Amination of branched aldehydes with azadicarboxylate was efficiently promoted by monoimide substituted cyclohexane-1,2-diamines, and the chiral quaternary amino aldehydes were successfully achieved in excellent yields (up to 99%) and enantioselectivities (up to 97% ee).
Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis
Liu, Chen,Zhu, Qiang,Huang, Kuo-Wei,Lu, Yixin
supporting information; experimental part, p. 2638 - 2641 (2011/07/08)
A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best ca
Primary amine catalyzed electrophilic amination of α,α- disubstituted aldehydes
Desmarchelier, Alaric,Yalgin, Hasret,Coeffard, Vincent,Moreau, Xavier,Greck, Christine
experimental part, p. 4430 - 4432 (2011/09/19)
Organocatalytic α-amination of α,α-disubstituted aldehydes promoted by 9-amino-(9-deoxy)-epi-quinine is described. α-Hydrazino aldehydes bearing a quaternary stereogenic center are obtained in good to excellent yields and enantioselectivities.
Highly efficient and practical pyrrolidine-camphor-derived organocatalysts for the direct α-amination of aldehydes
Liu, Pang-Min,Magar, Dhananjay R.,Chen, Kwunmin
supporting information; experimental part, p. 5705 - 5713 (2011/01/05)
A series of pyrrolidine-camphor-derived organocatalysts (1-4) were designed and synthesised. These organocatalysts were used for direct α-amination of aldehydes with dialkyl azodicarboxylates to give the desired α-aminated products in high chemical yields
Proline-catalysed asymmetric amination of α,α-disubstituted aldehydes: Synthesis of configurationally stable enantioenriched α-aminoaldehydes
Vogt, Henning,Vanderheiden, Sylvia,Braese, Stefan
, p. 2448 - 2449 (2007/10/03)
Proline-catalysed animation of α,α-disubstituted racemic aldehydes with azodicarboxylates proceeds smoothly to give configurationally stable scalemic aldehydes and oxazolidinones in up to 86% ee.
