title: An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: generality, applications and mechanistic investigations.
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.
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews KY16 9ST, UK. ads10@st-andrews.ac.uk.
authors.forename: Edward
authors.initials: E
authors.lastname: Richmond
authors.forename: Kenneth B
authors.initials: KB
authors.lastname: Ling
authors.forename: Nicolas
authors.initials: N
authors.lastname: Duguet
authors.forename: Lois B
authors.initials: LB
authors.lastname: Manton
authors.forename: Nihan
authors.initials: N
authors.lastname: Çelebi-Ölçüm
authors.forename: Yu-Hong
authors.initials: YH
authors.lastname: Lam
authors.forename: Sezen
authors.initials: S
authors.lastname: Alsancak
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D003500:Cyclization; D005030:Ethylenes / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry; D000078183:Oxindoles; D011789:Quantum Theory
chemical_list: D005030:Ethylenes; D007211:Indoles; D007659:Ketones; D009589:Nitrogen Oxides; D000078183:Oxindoles; C015388:nitrones; C022960:2-oxindole; C008223:ketene