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- Title
Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.
- Authors
Wu, Hongmiao; Zi, Weiwei; Li, Guigen; Lu, Hongjian; Toste, F. Dean
- Abstract
An enantioselective alkoxylation/Claisen rearrangement reaction was achieved by a strategic desymmetrization of 1,4-dienes under the catalysis of ( S)-DTBM-Segphos(AuCl)2/AgBF4. This reaction system was highly selective for the formation of 3,3-rearrangement products, providing cycloheptenes with various substitutions in good yield and good to excellent enantioselectivity. This transformation was further extended to bicyclic ring substrates, providing the opportunity to easily assemble 5,6- and 6,7-fused ring systems.
- Subjects
GOLD catalysts; DIOLEFINS; ALKOXYLATION; ENANTIOSELECTIVE catalysis; CLAISEN rearrangement; CYCLOHEPTENE
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 29, p8529
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201503357