title: Asymmetric access to the smallest enolate intermediate via organocatalytic activation of acetic ester.
abstract: An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and α,β-unsaturated imines to give α-unsubstituted δ-lactones and lactams, respectively.
authors.affiliation: Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.
authors.forename: Shaojin
authors.initials: S
authors.lastname: Chen
authors.forename: Lin
authors.initials: L
authors.lastname: Hao
authors.forename: Yuexia
authors.initials: Y
authors.lastname: Zhang
authors.forename: Bhoopendra
authors.initials: B
authors.lastname: Tiwari
authors.forename: Yonggui Robin
authors.initials: YR
authors.lastname: Chi
mesh_terms: D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D007097:Imines / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000085:Acetates; D004952:Esters; D007097:Imines; D007769:Lactams; D007783:Lactones; D014230:Triazoles