Asymmetric Reduction of Lactam-based β-Aminoacrylates. Synthesis of Heterocyclic β2-Amino Acids

Hugo Rego Campello, Jeremy S. Parker, Matthew W D Perry, Per Ryberg, Timothy Gallagher

Research output: Contribution to journalArticle (Academic Journal)peer-review

10 Citations (Scopus)
328 Downloads (Pure)

Abstract

The ability to affect asymmetric reduction of heterocyclic β-aminoacrylates 1 (n = 1–3) has been assessed with pyrrolidine and piperidone variants generating the corresponding N-heterocyclic β2-amino acids 3b and 5b with high enantioselectivity (≥97% ee) using a Rh/WALPHOS catalyst combination. The use of the carboxylic acid substrate was essential; the corresponding esters do undergo reduction but led to racemic products. The seven-ring azepanone variant (as the carboxylic acid 9b) underwent reduction, but only a minimal level of asymmetric induction was observed.
Original languageEnglish
Pages (from-to)4124–4127
Number of pages4
JournalOrganic Letters
Volume18
Issue number16
Early online date10 Aug 2016
DOIs
Publication statusPublished - 19 Aug 2016

Keywords

  • Asymmetric reduction

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