Enantioselective synthesis of α,α-disubstituted amines from nitroalkenes
Disubstituted nitroalkenes were converted into enantiomerically enriched amines (isolated as their hydrochloride salts) with enantiometric excesses of 88 to >95% in there steps: (a) highly stereoselective conjugate addition of the potassium salt of 4-phenyloxazolidin-2-one; (b) radical-mediated removal of the nitro group; (c) cleavage of the oxazolidinone.
Leroux, Mary-Lorene,Le Gall, Thierry,Mioskowski, Charles
p. 1817 - 1823
(2007/10/03)
SYNTHESIS OF THE RACEMIC FORM OF (Z)-1,17-DIAMINOOCTADEC-9-ENE, AN ALIPHATIC DIAMINE FROM COCCINELLIDAE. DETERMINATION OF THE ABSOLUTE CONFIGURATION OF THE (+)-NATURALLY-OCCURRING ANTIPODE
The total synthesis of the title compound (1) has been achieved.Also reported is the use of lanthanide induced shifts in 1H NMR spectroscopy to assign the absolute configuration of the α-carbon atom in chiral primary α-methylalkylamines.Application of this empirical method to natural (+)-1 shows that it has the R-configuration at C-17.
Braconnier, M.F.,Braekman, J.C.,Daloze, D.
p. 605 - 614
(2007/10/02)
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