Efficient and Highly Selective Synthesis of Enantiopure cis- or trans-3,4-Disubstituted 1,2,3,4-Tetrahydroisoquinolines

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 H3PO4·BF3 complex, under mild reaction conditions, is reported. Both enantiopure diastereoisomers (3S,4S)- and (3S,4R)-3-alky...

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Veröffentlicht in:Organic letters 2009-08, Vol.11 (16), p.3750-3753
Hauptverfasser: Concellón, José M, Tuya, Paula, del Solar, Virginia, García-Granda, Santiago, Díaz, M. Rosario
Format: Artikel
Sprache:eng
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Catalysis
Epoxy Compounds - chemistry
Molecular Structure
Stereoisomerism
Tetrahydroisoquinolines - chemical synthesis
Tetrahydroisoquinolines - chemistry
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container_end_page 3753
container_issue 16
container_start_page 3750
container_title Organic letters
container_volume 11
creator Concellón, José M
Tuya, Paula
del Solar, Virginia
García-Granda, Santiago
Díaz, M. Rosario
description 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.
doi_str_mv 10.1021/ol901388e
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subjects Catalysis
Epoxy Compounds - chemistry
Molecular Structure
Stereoisomerism
Tetrahydroisoquinolines - chemical synthesis
Tetrahydroisoquinolines - chemistry
title Efficient and Highly Selective Synthesis of Enantiopure cis- or trans-3,4-Disubstituted 1,2,3,4-Tetrahydroisoquinolines
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