1227182-01-5Relevant articles and documents
An efficient and enantioselective Michael addition of aromatic oximes to α,β-unsaturated aldehydes promoted by a chiral diamine catalyst derived from α,α-diphenyl prolinol
Chen, Feng,Ren, Hong-Xia,Yang, Yu,Ji, Shan-Ping,Zhang, Zheng-Bing,Tian, Fang,Peng, Lin,Wang, Li-Xin
, p. 369 - 375 (2017)
Chiral diamine catalysts 11a–e derived from α,α-diphenyl prolinol were prepared and successfully applied to the Michael addition of aromatic oximes to α,β-unsaturated aldehydes in mediocre to good yields (up to 78%) and good to high enantioselectivities (up to 93% ee).
In search of diamine analogs of the α,α-diphenyl prolinol privileged chiral organocatalyst. Synthesis of diamine derivatives of α,α-diphenyl-(S)-prolinol and their application as organocatalysts in the asymmetric Michael and Mannich reactions
Reyes-Rangel, Gloria,Vargas-Caporali, Jorge,Juaristi, Eusebio
supporting information, p. 379 - 391 (2015/12/31)
This paper describes improved reaction conditions for the substitution of the hydroxyl group in (S)-diphenyl(pyrrolidin-2-yl)methanol by the azide group, which was then reduced to the diamine derivative. We examined two protecting groups (N-Bn and N-Boc) on the pyrrolidine nitrogen in order to functionalize the primary amino group into various amide, alkylated amine, sulfonamide, thiourea and triazole derivatives. Notably, carefully controlled conditions were required to generate the desired derivatives from the sterically hindered benzhydrylamine moiety. Unexpectedly, upon removal of the N-protecting group in derivatives containing electrophilic polar double bonds (C=S, C=O) cyclization took place, affording products such as amidines. The target compounds were evaluated as bifunctional organocatalysts in the asymmetric Michael and Mannich addition reactions. (S)-2-(Azidodiphenylmethyl)pyrrolidine (S)-7 was identified as the most efficient organocatalyst among the various diamine derivatives of α,α-diphenyl-(S)-prolinol prepared in this work.
(S)-proline-derived catalysts for the acylative kinetic resolution of alcohols: A remote structural change allows a complete selectivity switch
Gleeson, Oliver,Gun'Ko, Yurii K.,Connon, Stephen J.
supporting information, p. 1728 - 1734 (2013/09/02)
A systematic preliminary study has identified a suite of catalysts, all readily prepared and derived from (S)-proline, which differ by a remote substituent only. If this substituent is capable of hydrogen-bond donation the catalyst will promote the resolu
