title: Synthesis and C-alkylation of hindered aldehyde enamines.
abstract: A new reactivity mode of hindered lithium amides with terminal epoxides is described whereby aldehyde enamines are produced via a previously unrecognized reaction pathway. Some of these aldehyde enamines display unprecedented C-alkylation reactivity toward unactivated primary and secondary alkyl halides. For comparison, the reactivity of aldehyde enamines synthesized via a traditional condensation method was examined. C- rather than N-alkylation was the dominant reaction pathway found with a range of electrophiles, making this route to alpha-alkylated aldehydes more synthetically useful than previously reported.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
authors.forename: David M
authors.initials: DM
authors.lastname: Hodgson
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Bray
authors.forename: Nicholas D
authors.initials: ND
authors.lastname: Kindon
authors.forename: Nigel J
authors.initials: NJ
authors.lastname: Reynolds
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Coote
authors.forename: Joann M
authors.initials: JM
authors.lastname: Um
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000577:Amides / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000577:Amides; D004852:Epoxy Compounds; D009942:Organometallic Compounds; D008094:Lithium