151416-29-4Relevant articles and documents
A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions
Zhao, Jinlong,Niu, Songtao,Jiang, Xi,Jiang, Yongwen,Zhang, Xiaojing,Sun, Tiemin,Ma, Dawei
, p. 6589 - 6599 (2018/05/31)
The amide derived from 4-hydroxy-l-proline and 2,6-dimethylaniline is a powerful ligand for Cu-catalyzed coupling of (hetero)aryl halides with sulfinic acid salts, allowing the formation of a wide range of (hetero)aryl sulfones from the corresponding (hetero)aryl halides at considerably low catalytic loadings. The coupling of (hetero)aryl iodides and sodium methanesulfinate proceeds at room temperature with only 0.5 mol % CuI and ligand, representing the first example for Cu-catalyzed arylation at both low catalytic loading and room temperature.
Highly diastereo- And enantioselective aldol reactions in common organic solvents using N-arylprolinamides as organocatalysts with enhanced acidity
Moorthy, Jarugu Narasimha,Saha, Satajit
experimental part, p. 739 - 748 (2009/07/19)
A broad set of N-arylprolinamides 1-8 with increasing NH acidity and steric crowding has been synthesized and its catalytic activity explored for enantioselective aldol reactions. In DMF containing 10 mol-% of TFA, all arylamides are found to catalyze the reaction between cyclohexanone and a variety of electrophilic aldehydes leading to aldols in excess of 90% yield and >95 % enantioselectivity. The per-fluorophenyl catalyst 8 is found to perform best with a broad substrate scope as compared to all other N-arylamides 1-7. It is shown that 8 can indeed be employed in highly nonpolar as well as polar solvents including brine to afford high yields of aldols with excellent diastereo- as well as enantio-selectivity. The results observed for 8 are amongst the best reported so far for prolinamides that do not contain additional stereogenic center(s) and hydrogen-bonding site(s). The molecular structures of 7 and 8, determined by X-ray crystallography and presumed to reflect the most stable conformations, reveal a notable difference in the conformations of the N-aryl rings; the aryl ring exhibits tendency to lie coplanar with the amide functionality in the case of 7, while the per- fluorophenyl ring twists almost orthogonally with respect to the plane of the amide of functionality in 8. The superior performance of the latter is attributed to, in addition to the enhanced NH acidity, the tendency of the perfluorophenyl ring to lie orthogonally to the amide group, which may facilitate a stronger binding of the electrophilic aldehyde via hydrogen bonding in the transition state.
Asymmetric intramolecular Michael reaction catalyzed by proline-derived small anilides
Kikuchi, Makoto,Inagaki, Tomohiko,Nishiyama, Hisao
, p. 1075 - 1078 (2008/02/13)
Simple proline-derived anilide-catalyzed asymmetric intramolecular Michael reaction was described. Chiral cyclic ketoaldehydes were obtained from acyclic formyl enones in excellent yields with good stereoselectivity. The reaction proceeded in exceptionall
