Efficient and highly selective synthesis of enantiopure cis- or trans-3,4-disubstituted 1,2,3,4-tetrahydroisoquinolines.
An efficient synthesis of enantiopure 3,4-disubstituted 1,2,3,4-tetrahydroisoquinolines, by treatment of readily available (2R,1'S)- or (2S,1'S)-2-(1-aminoalkyl)epoxides with H(3)PO(4).BF(3) complex, under mild reaction conditions, is reported. Both enantiopure diastereoisomers (3S,4S)- and (3S,4R)-3-alkyl-4-hydroxymethyl-1,2,3,4-tetrahydroisoquinolines were available starting from the suitable syn- or anti-aminoepoxide, respectively. A mechanism based on an intramolecular Friedel-Crafts-type reaction has been proposed to explain these results.
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Spain. jmcg@uniovi.es
Tuya
Paula
P
del Solar
Virginia
V
García-Granda
Santiago
S
Díaz
M Rosario
MR
D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
D004852:Epoxy Compounds; D044005:Tetrahydroisoquinolines