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ChemInform Abstract: Pictet—Spengler Condensation of N-Sulfonyl-β-phenethylamines with α-Chloro-α-phenylselenoesters. New Synthesis of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylates.

✍ Scribed by Claudio C. Silveira; Carmem R. Bernardi; Antonio L. Braga; Teodoro S. Kaufman

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199938148

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✦ Synopsis

Pictet-Spengler Condensation of N-Sulfonyl-β-phenethylamines with α-Chloro-α-phenylselenoesters.

New Synthesis of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylates.

-Lewis acid promoted Pictet-Spengler type condensation of the tosylated β-phenethylamines (I) with α-chloro-α-seleno carboxylates (II) directly yields the tetrahydroisoquinoline-1carboxylates (III). Various degrees of diastereoselection can be obtained using chiral sulfonamides and/or esters as the substrates. -(SILVEIRA, CLAU-

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