35046-48-1Relevant academic research and scientific papers
Catalytic, enantioselective N-acylation of lactams and thiolactams using amidine-based catalysts
Yang, Xing,Bumbu, Valentina D.,Liu, Peng,Li, Ximin,Jiang, Hui,Uffman, Eric W.,Guo, Lei,Zhang, Wei,Jiang, Xuntian,Houk,Birman, Vladimir B.
supporting information, p. 17605 - 17612 (2013/01/15)
In contrast to alcohols and amines, racemic lactams and thiolactams cannot be resolved directly via enzymatic acylation or classical resolution. Asymmetric N-acylation promoted by amidine-based catalysts, particularly Cl-PIQ 2 and BTM 3, provides a convenient method for the kinetic resolution of these valuable compounds and often achieves excellent levels of enantioselectivity in this process. Density functional theory calculations indicate that the reaction occurs via N-acylation of the lactim tautomer and that cation-π interactions play a key role in the chiral recognition of lactam substrates.
Stereocontrol between remote atom centers in acyclic substrates. Anti addition of hydride to 1,5-, 1,6-, and 1,7-hydroxy ketones
Zhang, Han-Cheng,Harris, Bruce D.,Costanzo, Michael J.,Lawson, Edward C.,Maryanoff, Cynthia A.,Maryanoff, Bruce E.
, p. 7964 - 7981 (2007/10/03)
For conformationally unconstrained, acyclic organic compounds, the control of stereogenic centers at remote positions of a chain, that is, at a distance of four or more atom centers, remains a challenging problem in asymmetric synthesis. We report on our
Efficient Routes to Chiral 2-Substituted and 2,6-Disubstituted Piperidines
Katritzky, Alan R.,Qiu, Guofang,Yang, Baozhen,Steel, Peter J.
, p. 6699 - 6703 (2007/10/03)
The syntheses of chiral 2-substituted and 2,6-disubstituted piperidines, and piperidin-2-ylphosphonates, via benzotriazole methodology are described.
ALKYLATION OF N-TRIMETHYLSILYLATED PRIMARY AMINES WITH ARYLETHYLENE OXIDES. AN EFFICIENT SYNTHESIS OF 1-PHENETHANOLAMINES.
Atkins, Randall K.,Frazier, Jeffery,Moore, Larry L.,Weigel, Leland O.
, p. 2451 - 2454 (2007/10/02)
Reaction of unhindered N-trimethylsilylated primary amines with styrene oxide derivatives provides good yields of 1-phenethanolamines after acidic hydrolysis during work-up.This methodology results in much better conversions and higher yields when compare
