An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: generality, applications and mechanistic investigations

Edward Richmond, Kenneth Bruce Ling, Nicolas Fabien Denis Duguet, Lois B. Manton, Nihan Çelebi-Ölçüm, Yu-hong Lam, Sezen Alsancak, Alexandra Martha Zoya Slawin, K. N. Houk, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)
8 Downloads (Pure)

Abstract

The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.
Original languageEnglish
Pages (from-to)1807-1817
Number of pages11
JournalOrganic & Biomolecular Chemistry
Volume13
Issue number6
Early online date12 Dec 2014
DOIs
Publication statusPublished - 14 Feb 2015

Keywords

  • Amino acids
  • Anti-cancer agents
  • Cascade process
  • Computational investigation
  • L-serine
  • Potential utility

Fingerprint

Dive into the research topics of 'An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: generality, applications and mechanistic investigations'. Together they form a unique fingerprint.

Cite this