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- Title
Desilylation-Activated Propargylic Transformation: Enantioselective Copper-Catalyzed [3+2] Cycloaddition of Propargylic Esters with β-Naphthol or Phenol Derivatives.
- Authors
Shao, Long; Wang, Ya ‐ Hui; Zhang, De ‐ Yang; Xu, Jie; Hu, Xiang ‐ Ping
- Abstract
A copper-catalyzed asymmetric [3+2] cycloaddition of 3-trimethylsilylpropargylic esters with either β-naphthols or electron-rich phenols has been realized and proceeds by a desilylation-activated process. Under the catalysis of Cu(OAc)2⋅H2O in combination with a structurally optimized ketimine P,N,N-ligand, a wide range of optically active 1,2-dihydronaphtho[2,1-b]furans or 2,3-dihydrobenzofurans were obtained in good yields and with high enantioselectivities (up to 96 % ee). This represents the first desilylation-activated catalytic asymmetric propargylic transformation.
- Subjects
ESTERS; COPPER catalysts; PHENOL derivatives; NAPHTHOL derivatives; RING formation (Chemistry); STEREOSELECTIVE reactions
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 16, p5098
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201510793