From Triazoles to Imidazolines through the Sequential N-H Insertion of alpha-Imino Rhodium-Carbenes into beta-Enamino Esters/Enamine-Imine Tautomerization/Conjugate Addition Cascade
- 등재 SCIE, SCOPUS
- 발행기관 AMER CHEMICAL SOC
- 발행년도 2014
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000112905
- 본문언어 영어
- Published As http://dx.doi.org/10.1021/jo501785d
초록/요약
A rhodium(II)-catalyzed denitrogenative coupling of N-sulfonyl-1,2,3-triazoles with ambiphilic beta-enamino esters affords 2,5-dihydro-H-1-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 alpha-imino rhodium-carbene, followed by enamine-imine tautomerization and conjugate addition. Moreover, the reaction proceeds with high diastereoselectivity for alpha-substituted beta-enamino esters (R-3 = Me, Ph) to give a single diastereomer.
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