5930-98-3Relevant articles and documents
Merging Asymmetric [1,2]-Additions of Lithium Acetylides to Carbonyls with Type II Anion Relay Chemistry
O'brien, Kevin T.,Smith, Amos B.
, p. 7655 - 7659 (2019)
An enantioselective three-component coupling reaction has been developed, enabling the union of a variety of lithium acetylides and electrophiles exploiting an achiral linchpin via an anionic reaction cascade. This Type II Anion Relay Chemistry tactic is initiated via an enantioselective [1,2]-carbonyl addition exploiting BINOL catalysis to access an enantioenriched alkoxide intermediate. Migration of charge across the linchpin via a [1,4]-Brook rearrangement with electrophile capture affords a three-component propargyl ether adduct. Herein, we report the development, scope, and limitations of this reaction sequence.
Phosphine-Catalyzed Intermolecular Annulations of Fluorinated ortho-Aminophenones with Alkynones – The Switchable [4+2] or [4+2]/[3+2] Cycloaddition
Zhang, Yanshun,Sun, Yaoliang,Wei, Yin,Shi, Min
supporting information, p. 2129 - 2135 (2019/03/13)
A phosphine-catalyzed intermolecular annulation reaction of functionalized ortho-aminoacetophenones with alkynones has been disclosed in this paper. A variety of 2-alkynylquinolines and benzo-fused indolizine were selectively afforded in moderate to good yields at different reaction temperatures and with different phosphine catalysts via the in situ generated zwitterionic intermediate derived from alkynone and phosphine. (Figure presented.).
Aerobic oxidation of propargylic alcohols to αβ,-unsaturated alkynals or alkynones catalyzed by fe(NOH, TEMPO and sodium chloride in toluene
Liu, Jinxian,Xie, Xi,Ma, Shengming
experimental part, p. 1569 - 1576 (2012/06/30)
A practical aerobic oxidation of propargylic alcohols using Fe(NOH, TEMPO and sodium chloride in toluene at room temperature was applied to various type of propargylic alcohols affording ,-unsaturated alkynals or alkynones in good to excellent yields. This protocol could be applied in academic laboratories as well as in industrial-scale production.