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Efficient and highly selective synthesis of enantiopure cis-or trans-3,4-disubstituted 1,2,3,4-tetrahydroisoquinolines

Author:
Concellón Gracia, José ManuelUniovi authority; Tuya Sánchez, PaulaUniovi authority; Solar, Virginia del; García-Granda, SantiagoUniovi authority; Díaz Fernández, María del RosarioUniovi authority
Publication date:
2009
Publisher version:
http://dx.doi.org/10.1021/ol901388e
Citación:
Organic Letters, 11 (16), p. 3750-3753 (2009); doi:10.1021/ol901388e
Descripción física:
p. 3750-3753
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 H3PO4·BF3 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.

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 H3PO4·BF3 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.

URI:
http://hdl.handle.net/10651/7976
ISSN:
1523-7060
Identificador local:

20090380

DOI:
10.1021/ol901388e
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