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 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol901388e |