Sequential Pd-catalyzed asymmetric allene diboration/alpha-aminoallylation.
Pd-catalyzed enantioselective diboration of prochiral allenes provides adducts which participate in highly selective allylation reactions with primary imines. The allylation product is a vinyl boronate which may be oxidized to give nonracemic Mannich products (87-97% ee). Alternatively, enantiomerically enriched homoallylic amine derivatives may be obtained by protonation and Suzuki cross-coupling of the vinyl boronate.
Sieber
Joshua D
JD
Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
Morken
James P
JP
D000466:Alkadienes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis*; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis*; D008958:Models, Molecular; D010165:Palladium / Q000737:chemistry
D000466:Alkadienes; D000498:Allyl Compounds; D000588:Amines; D001880:Boranes; D007659:Ketones; C025947:propadiene; D010165:Palladium