Enantiomerically pure tetrahydroisoquinolines by enzyme catalysis and gold-catalyzed phenol synthesis |
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Authors: | A Stephen K Hashmi Filiz Ata Patrick Haufe Frank Rominger |
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Institution: | Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany |
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Abstract: | Five different furfural derivatives were converted to chiral cyanohydrins by enzyme catalysis in good enantiomeric excess. After a sequence of silyl protection, nitrile reduction, tosylation and propargylation, substrates for the gold(I) catalyzed cycloisomerization of δ-alkynyl furans delivered good yields of enantiomerically pure dihydroxytetrahydroisoquinoline building blocks. Neither racemization nor elimination to quinolines was observed. |
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