1029604-06-5Relevant academic research and scientific papers
Enantioselective boronate additions to N-acyl quinoliniums catalyzed by tartaric acid
Kodama, Tomohiro,Moquist, Philip N.,Schaus, Scott E.
, p. 6316 - 6319 (2011)
Tartaric acid catalyzes the asymmetric addition of vinylboronates to N-acyl quinoliniums, affording highly enantioenriched dihydroquinolines. The catalyst serves to activate the boronate through a ligand-exchange reaction and generates the N-acyl quinolinium in situ from the stable quinoline-derived N,O-acetal.
Asymmetric petasis reactions catalyzed by chiral biphenols
Lou, Sha,Schaus, Scott E.
, p. 6922 - 6923 (2008/09/21)
Chiral biphenols catalyze the enantioselective Petasis reaction of alkenyl boronates, secondary amines, and ethyl glyoxylate. The reaction requires the use of 15 mol % of (S)-VAPOL as the catalyst, alkenyl boronates as nucleophiles, ethyl glyoxylate as the aldehyde component, and 3 A molecular sieves as an additive. The chiral α-amino ester products are obtained in good yields (71-92%) and high enantiomeric ratios (89:11-98:2). Mechanistic investigations indicate single ligand exchange of acyclic boronate with VAPOL and tetracoordinate boronate intermediates. Copyright
