Functional primary amines and diamines from alpha-aminoacids. a concise route to substituted 2-aminotetralins.
S-Phthalimidomethyl xanthates derived from various alpha-amino acids add efficiently to a range of unactivated alkenes to give a variety of highly functionalized, protected amines. In the case of phenylalanine and tyrosine derived xanthates, the adducts can be further converted into the rare 4-substituted 2-aminotetralines by a radical ring closure onto the aromatic ring.
Quiclet-Sire
Béatrice
B
Laboratoire de Synthese Organique, CNRS UMR 7652, Ecole Polytechnique, 91128 Palaiseau Cedex, France.
Revol
Guillaume
G
Zard
Samir Z
SZ
D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003959:Diamines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D000596:Amino Acids; D003959:Diamines; D013764:Tetrahydronaphthalenes; C006561:2-aminotetralin