CuI/RhII-Catalyzed Tandem Convergent Multicomponent Reaction for the Regio- and Stereocontrolled Synthesis of γ-Oxo-β-amino Esters

Da Jung Jung, Hyun Ji Jeon, Joo Hyun Lee, Sang Gi Lee

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

The first example of a highly regio- and stereoselective catalytic method for the three-component one-pot synthesis of highly functionalized α-vinylated γ-oxo-β-amino esters is disclosed. In this catalytic triad, the CuI-catalyst selectively catalyzes the cycloaddition of the 1-alkyne and sulfonyl azide first resulting in the corresponding 1-sulfonyl-1,2,3-triazole. An α-imino RhII-carbene is generated from an open-chain α-imino diazo of the triazole, and this species reacts with γ-hydroxy α,β-unsaturated esters to form allylic (Z)-amino vinyl ethers. Rapid deconjugative [3,3]-sigmatropic rearrangement affords the α-vinyl γ-oxo-β-amino esters in high yields with high levels of diastereoselectivity.

Original languageEnglish
Pages (from-to)3498-3501
Number of pages4
JournalOrganic Letters
Volume17
Issue number14
DOIs
StatePublished - 17 Jul 2015

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