Direct catalytic asymmetric three-component Kabachnik-fields reaction
(Chemical Equation Presented) As mimics of α-amino acids, α-amino phosphonates have great promise as antibacterial and anti-HIV agents as well as protease inhibitors. Racemic α-branched aldehydes react, in the presence the new chiral phosphoric acid catalyst 1, directly with p-anisidine (PMPNH2) and a phosphite to furnish β-branched α-amino phosphonates highly diastereoselectively and enantioselectively. Anth = anthracenyl.
Cheng, Xu,Goddard, Richard,Buth, Gernot,List, Benjamin
supporting information; experimental part
p. 5079 - 5081
(2009/03/11)
Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions: Synthetic and Mechanistic Insights
Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 °C. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.
Coe, Jotham W.,Bianco, Krista E.,Boscoe, Brian P.,Brooks, Paige R.,Cox, Eric D.,Vetelino, Michael G.
p. 9964 - 9970
(2007/10/03)
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