Abstract
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.
Original language | English |
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Pages (from-to) | 17605-17612 |
Number of pages | 8 |
Journal | Journal of the American Chemical Society |
Volume | 134 |
Issue number | 42 |
DOIs | |
State | Published - Oct 24 2012 |