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- Title
Regioselective α-Addition of Deconjugated Butenolides: Enantioselective Synthesis of Dihydrocoumarins.
- Authors
Wu, Bo; Yu, Zhaoyuan; Gao, Xiang; Lan, Yu; Zhou, Yong ‐ Gui
- Abstract
The enantioselective α-addition of deconjugated butenolides has rarely been exploited, in contrast to the well-studied γ-addition of deconjugated butenolides. In this study, an unprecedented asymmetric α-addition/transesterification of deconjugated butenolides with ortho-quinone methides generated in situ afforded a series of functionalized 3,4-dihydrocoumarins containing two contiguous stereogenic centers with excellent diastereo- and enantioselectivity. DFT calculations suggested that the rarely observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic dienolate and the electrophilic ortho-quinone methide.
- Subjects
BUTENOLIDES synthesis; COUMARINS; HETEROCYCLIC compounds synthesis; ASYMMETRIC synthesis; ENANTIOSELECTIVE catalysis; REGIOSELECTIVITY (Chemistry); NUCLEOPHILIC addition (Chemistry); QUINONE methides; TRANSESTERIFICATION
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 14, p4064
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201700437