Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 14, Pages 4006-4010Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700437
Keywords
asymmetric catalysis; butenolides; dihydrocoumarins; nucleophilic addition; ortho-quinone methides
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Funding
- National Natural Science Foundation of China [21532006, 21372220]
- Strategic Priority Program of Chinese Academy of Sciences [XDB17020300]
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The enantioselective alpha-addition of deconjugated butenolides has rarely been exploited, in contrast to the well-studied gamma-addition of deconjugated butenolides. In this study, an unprecedented asymmetric alpha-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.
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