Article ID Journal Published Year Pages File Type
5227291 Tetrahedron 2009 9 Pages PDF
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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Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry