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Synergistic Pd(0)/Rh(II) Dual Catalytic [6 + 3] Dipolar Cycloaddition for the Synthesis of Monocyclic Nine-Membered N,O-Heterocycles and Their Alder-ene Rearrangement to Fused Bicyclic Compounds
- Title
- Synergistic Pd(0)/Rh(II) Dual Catalytic [6 + 3] Dipolar Cycloaddition for the Synthesis of Monocyclic Nine-Membered N,O-Heterocycles and Their Alder-ene Rearrangement to Fused Bicyclic Compounds
- Authors
- Lee K.R.; Ahn S.; Lee S.-G.
- Ewha Authors
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- SCOPUS Author ID
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- Issue Date
- 2021
- Journal Title
- Organic Letters
- ISSN
- 1523-7060
- Citation
- Organic Letters vol. 23, no. 9, pp. 3735 - 3740
- Publisher
- American Chemical Society
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- The catalytic construction of a monocyclic medium-sized N,O-heterocyclic ring represents a formidable challenge in organic synthesis. Herein we report the synergistic palladium(0)/rhodium(II) dual catalytic cycloaddition of vinylpropylene carbonates with N-sulfonyl-1,2,3-triazoles to afford monocyclic nine-membered N,O-heterocycles. The catalytically generated 1,6-dipole-equivalent zwitterionic π-allyl palladium(II) complex and the 1,3-dipole-equivalent α-imino rhodium(II) carbenoid intermediate react with each other in a formal [6 + 3] dipolar cycloaddition to furnish nine-membered oxazonines, which can be transformed into cis-fused [4.3.0] bicyclic compounds via a transannular Alder-ene rearrangement. The tandem one-pot cycloaddition/Alder-ene rearrangement sequence is also possible. © 2021 American Chemical Society.
- DOI
- 10.1021/acs.orglett.1c01135
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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