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  • Title: Efficient and highly selective synthesis of enantiopure cis- or trans-3,4-disubstituted 1,2,3,4-tetrahydroisoquinolines.
    Author: Concellón JM, Tuya P, del Solar V, García-Granda S, Díaz MR.
    Journal: Org Lett; 2009 Aug 20; 11(16):3750-3. PubMed ID: 19627107.
    Abstract:
    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.
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