Aldehyde selective Wacker oxidations of phthalimide protected allylic amines: a new catalytic route to beta3-amino acids.
A new method for the synthesis of beta(3)-amino acids is presented. Phthalimide protected allylic amines are oxidized under Wacker conditions selectively to aldehydes using PdCl(2) and CuCl or Pd(MeCN)(2)Cl(NO(2)) and CuCl(2) as complementary catalyst systems. The aldehydes are produced in excellent yields and exhibit a large substrate scope. Beta-amino acids and alcohols are synthesized by oxidation or reduction and subsequent deprotection.
Weiner
Barbara
B
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Baeza
Alejandro
A
Jerphagnon
Thomas
T
Feringa
Ben L
BL
D000447:Aldehydes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry* / Q000145:classification; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D010797:Phthalimides / Q000737:chemistry*
D000447:Aldehydes; D000498:Allyl Compounds; D000588:Amines; D000596:Amino Acids; D010797:Phthalimides; C037431:phthalimide; D010165:Palladium