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Updated: Aug 11, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis
1Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.
Abstract:
The vinylogous Mannich reaction is rapidly emerging as an important process for the construction of derivatives of delta-aminocarbonyl compounds. Because the iminium and dienol components employed in this addition may be either acyclic or cyclic, a wide variety of adducts may be quickly assembled. These intermediates may then in turn be converted into a broad array of alkaloids and substituted nitrogen heterocycles. We have developed a number of variations of this reaction and have applied some of them to the concise syntheses of a number of structurally diverse and complex alkaloid natural products. Many of these results are presented in a historical context in this Account.
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