Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 38, Pages 10223-10227Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405857
Keywords
2,3-dihydrofurans; asymmetric catalysis; copper; cycloadditions; synthetic methods
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Funding
- Dalian Institute of Chemical Physics (CAS)
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An enantioselective synthesis of highly functionalized dihydrofurans through a copper-catalyzed asymmetric [3+2] cycloaddition of beta-ketoesters with propargylic esters has been developed. With a combination of Cu(OTf)(2) and a chiral tridentate P, N, N ligand as the catalyst, a variety of 2,3-dihydrofurans bearing an exocyclic double bond at the 2 position were obtained in good chemical yields and with good to high enantioselectivities. The exocyclic double bond can be hydrogenated in a highly diastereoselective fashion to give unusual cis-2,3-dihydrofuran derivatives, thus further enhancing the scope of this transformation.
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