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Elsevier, Tetrahedron Letters, 32(44), p. 6137-6140

DOI: 10.1016/s0040-4039(03)01452-7

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Thioorthoesters in the activated Pictet–Spengler cyclization. Synthesis of 1-thiosubstituted tetrahydroisoquinolines and carboncarbon bond formation via sulfonyl iminium ions generated from N,S-sulfonyl acetals

Journal article published in 2003 by Claudio C. Silveira, Carmem R. Bernardi, Antonio L. Braga ORCID, Teodoro S. Kaufman ORCID
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This paper is available in a repository.

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Abstract

The elaboration of 1-alkylthio- and 1-arylthio-tetrahydroisoquinolines by means of the activated Pictet–Spengler reaction of N-sulfonyl-β-phenethylamines with thioorthoesters as electrophiles, and their use as sulfonyl iminium ion precursors for carboncarbon bond formation, leading to 1-substituted tetrahydroisoquinoline derivatives, is reported.