481038-59-9Relevant articles and documents
Using the competing enantioselective conversion method to assign the absolute configuration of cyclic amines with BODE’s acylation reagents
Dooley, Charles J.,Burtea, Alexander,Mitilian, Christina,Dao, Wendy T.,Qu, Bo,Salzameda, Nicholas T.,Rychnovsky, Scott D.
, p. 10750 - 10759 (2020/10/02)
The competing enantioselective conversion (CEC) method is a quick and reliable means to determine absolute configuration. Previously, Bode’s chiral acylated hydroxamic acids were used to determine the stereochemistry of primary amines, as well as cyclic and acyclic secondary amines. The enantioselective acylation has been evaluated for 4-, 5-, and 6-membered cyclic secondary amines, including medicinally relevant compounds. The limitations of the method were studied through computational analysis and experimental results. Piperidines with substituents at the 2-position did not behave well unless the axial conformer was energetically accessible, which is consistent with the transition state geometries proposed by Bode and Kozlowski. Control experiments were performed to investigate the cause of degrading selectivity under the CEC reaction conditions. The present study expands the scope of the CEC method for secondary amines and provides a better understanding of the reaction profile.
Stereoelectronic basis for the kinetic resolution of n-heterocycles with chiral acylating reagents
Hsieh, Sheng-Ying,Wanner, Benedikt,Wheeler, Philip,Beauchemin, Andre M.,Rovis, Tomislav,Bode, Jeffrey W.
supporting information, p. 7228 - 7231 (2014/06/23)
The kinetic resolution of N-heterocycles with chiral acylating agents reveals a previously unrecognized stereoelectronic effect in amine acylation. Combined with a new achiral hydroxamate, this effect makes possible the resolution of various N-heterocycles by using easily prepared reagents. A transition-state model to rationalize the stereochemical outcome of this kinetic resolution is also proposed.
Catalytic asymmetric synthesis of substituted morpholines and piperazines
Zhai, Huimin,Borzenko, Andrey,Lau, Ying Yin,Ahn, Shin Hye,Schafer, Laurel L.
supporting information, p. 12219 - 12223 (2013/02/23)
Under two conditions: Hydroamination catalyzed by group 4 metals is featured in the modular and enantioselective synthesis of 3-substituted morpholines and the diastereoselective synthesis of 2,5-substituted piperazines. Copyright