title: Cu(I)/Rh(II)-Catalyzed Tandem Convergent Multicomponent Reaction for the Regio- and Stereocontrolled Synthesis of γ-Oxo-β-amino Esters.
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 Cu(I)-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 Rh(II)-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.
authors.affiliation: Department of Chemistry and Nano Science (BK Plus), Ewha Womans University, Seoul 120-750, Korea.
authors.forename: Da Jung
authors.initials: DJ
authors.lastname: Jung
authors.affiliation: Department of Chemistry and Nano Science (BK Plus), Ewha Womans University, Seoul 120-750, Korea.
authors.forename: Hyun Ji
authors.initials: HJ
authors.lastname: Jeon
authors.affiliation: Department of Chemistry and Nano Science (BK Plus), Ewha Womans University, Seoul 120-750, Korea.
authors.forename: Joo Hyun
authors.initials: JH
authors.lastname: Lee
authors.affiliation: Department of Chemistry and Nano Science (BK Plus), Ewha Womans University, Seoul 120-750, Korea.
authors.forename: Sang-gi
authors.initials: SG
authors.lastname: Lee
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D004952:Esters; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: C000602329:1-sulfonyl-1,2,3-triazole; D000596:Amino Acids; D004952:Esters; D014230:Triazoles; D014753:Vinyl Compounds; D003300:Copper; D012238:Rhodium