Catalytic, enantioselective N-acylation of lactams and thiolactams using amidine-based catalysts

Xing Yang, Valentina D. Bumbu, Peng Liu, Ximin Li, Hui Jiang, Eric W. Uffman, Lei Guo, Wei Zhang, Xuntian Jiang, K. N. Houk, Vladimir B. Birman

Research output: Contribution to journalArticlepeer-review

71 Scopus citations

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 languageEnglish
Pages (from-to)17605-17612
Number of pages8
JournalJournal of the American Chemical Society
Volume134
Issue number42
DOIs
StatePublished - Oct 24 2012

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