81802-33-7Relevant academic research and scientific papers
Enantioselective α-vinylation of aldehydes via the synergistic combination of copper and amine catalysis
Skucas, Eduardas,MacMillan, David W. C.
supporting information; experimental part, p. 9090 - 9093 (2012/07/14)
The enantioselective α-vinylation of aldehydes using vinyl iodonium triflate salts has been accomplished via the synergistic combination of copper and chiral amine catalysis. These mild catalytic conditions provide a direct route for the enantioselective construction of enolizable α-formyl vinylic stereocenters without racemization or olefin transposition. These high-value coupling adducts are readily converted into a variety of useful olefin synthons.
Enantioselective organo-SOMO catalysis: The α-vinylation of aldehydes
Kim, Hahn,MacMillan, David W. C.
, p. 398 - 399 (2008/09/20)
The first enantioselective organocatalytic α-vinylation of aldehydes has been accomplished. Selective oxidation of chiral enamines, derived from the condensation of aldehydes and a chiral secondary amine catalyst, leads to the production of highly reactive radical cations that exist in an asymmetric environment. These SOMO-activated species undergo direct coupling with readily available potassium organotrifluoroborate salts to yield enantioenriched α-vinyl aldehydes. The described reaction procedure achieves carbon-carbon bond formation in an efficient manner with consistently high levels of enantioinduction and geometrical control for the trans-olefin product. A wide range of both aldehydes and potassium organotrifluoroborate salts, including those typically susceptible to oxidative conditions, are accommodated under the reaction conditions. Results herein further demonstrate the capacity of the SOMO catalysis platform to achieve asymmetric carbon-carbon bond formations that are difficult to access via traditional methods. Copyright
Nickel(0)-catalyzed asymmetric hydrocyanation of 1,3-dienes
Saha, Biswajit,RajanBabu
, p. 4657 - 4659 (2007/10/03)
1,2-Bis-diarylphosphinites are excellent ligands for the Ni(0)-catalyzed hydrocyanation of certain types of 1,3-dienes. 1-Phenyl-1,3-butadiene, 1-vinyl-3,4-dihydronaphthalene, and 1-vinylindene undergo highly regioselective hydrocyanation under ambient co
