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Synfacts 2006(6): 0547-0547  
DOI: 10.1055/s-2006-934465
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Gold-Catalyzed Pictet-Spengler Reactions

Contributor(s): Victor Snieckus, Bärbel Wittel
S. W. Youn*
Pukyong National University, Busan, South Korea
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

An efficient gold(III)-catalyzed Pic­tet-Spengler synthesis of tetrahydroisoquinolines and tetrahydro-β-carbolines is presented. Of the several different metal salts and additives that were tested, gold(III) chloride with silver triflate showed the best conversions. Both electron-withdrawing and electron-donating R1 substituents as well as aromatic, saturated and α,β-unsaturated aliphatic and heterocyclic systems were well tolerated in the reaction.