Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 48, Pages 14447-14451Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508331
Keywords
allenes; desymmetrization; enantioselective synthesis; gold; hydroalkoxylation
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Funding
- NIHGMS [RO1 GM073932]
- College of Chemistry CheXray (NIH Shared Instrumentation Grant) [S10-RR027172]
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A gold(I)-catalyzed enantioselective desymmetrization of 1,3-diols was achieved by intramolecular hydroalkoxylation of allenes. The catalyst system 3-F-dppe(AuCl)(2)/(R)-C-8- TRIPAg proved to be specifically efficient to promote the desymmetrizing cyclization of 2-aryl-1,3-diols, which have proven challenging substrates in previous reports. Multisubstituted tetrahydrofurans were prepared in good yield with good enantioselectivity and diastereoselectivity by this method.
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