Organocatalyzed Enantioselective Direct Mannich Reaction of α-Styrylacetates
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Updated: Mar 20, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Jie Guang1, Saroj Rout1, Manisha Bihani1
1Department of Chemistry, University of Texas at San Antonio , One UTSA Circle, San Antonio, Texas 78249-0698, United States.
Abstract:
An organocatalyzed direct Mannich reaction of unactivated α-styrylacetates was realized for the first time. By using a quinidine-derived C6'-urea catalyst, the direct Mannich reaction of α-styrylacetates and N-tosylimines gave the desired β-amino esters in high yields, diastereoselectivities, and ee values. The reaction provides a highly stereoselective (up to 96:4 dr and 97% ee) and the most straightforward synthesis of functionalized N-tosylated β-amino esters. The products can be used as precursors for the highly selective synthesis of tetrahydrofuran derivatives.
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