Abstract
A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic β-enamino esters affords 2,5-dihydro-1H-imidazoles (3-imidazolines) with broad functional group tolerance. Mechanistic studies using a deuterium-labeled triazole suggest that the reaction proceeds in a cascade through the N-H insertion of an α-imino rhodium-carbene, followed by enamine-imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for α-substituted β-enamino esters (R3 = Me, Ph) to give a single diastereomer. (Chemical Equation Presented).
Original language | English |
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Pages (from-to) | 9865-9871 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 79 |
Issue number | 20 |
DOIs | |
State | Published - 17 Oct 2014 |
Bibliographical note
Publisher Copyright:© 2014 American Chemical Society.