The development of carbon-carbon bond forming reactions of aminal radicals
Aminal radicals were generated and used in synthetic reactions for the first time. Aminal radicals are formed from aminals by radical translocation using AIBN and a stoichiometric hydrogen atom donor, or by SmI2 reduction of N-acyl amidines or amidinium ions in the presence of a proton source. Aminal radicals were found to participate in inter- and intramolecular C-C bond forming reactions with electron deficient alkenes. Chemical yields were as high as 99%.
Schiedler, David A.,Vellucci, Jessica K.,Lu, Yi,Beaudry, Christopher M.
p. 1448 - 1465
(2015/02/19)
Reductive synthesis of aminal radicals for carbon-carbon bond formation
Aminal radicals were generated by reduction of the corresponding amidine or amidinium ion. The intermediate radicals participate in C-C bond-forming reactions to produce fully substituted aminal stereocenters. No toxic additives or reagents are required. More than 30 substrate combinations are reported, and chemical yields are as high as 99%.
Schiedler, David A.,Lu, Yi,Beaudry, Christopher M.
supporting information
p. 1160 - 1163
(2014/03/21)
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