alpha-Aminoallylation of aldehydes with ammonia: stereoselective synthesis of homoallylic primary amines.
Three-component reactions of aldehydes, ammonia, and allylboronates were found to provide homoallylic primary amines in high yields with high chemo- and stereoselectivities. A two-step, one-pot, stereoselective synthesis of an uncommon alpha-amino acid, alloisoleucine, was achieved utilizing this reaction.
Sugiura
Masaharu
M
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Hirano
Keiichi
K
Kobayashi
Shu
S
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D000641:Ammonia / Q000737:chemistry*; D007532:Isoleucine / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000447:Aldehydes; D000498:Allyl Compounds; D000588:Amines; D007532:Isoleucine; D000641:Ammonia