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Exploiting Distal Reactivity of Coumarins: A Rhodium‐Catalyzed Vinylogous Asymmetric Ring‐Opening Reaction
Author(s) -
Loh Charles C. J.,
Schmid Matthias,
Peters Brendan,
Fang Xiang,
Lautens Mark
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600654
Subject(s) - rhodium , chemistry , reactivity (psychology) , coumarin , aldol reaction , catalysis , ring (chemistry) , mannich reaction , enantioselective synthesis , combinatorial chemistry , stereochemistry , organic chemistry , medicine , alternative medicine , pathology
While the utility of vinylogous enolates is well established in the setting of vinylogous aldol, Mannich, and Michael chemistries, literature reports concerning γ‐reactivity are scarce for other reaction classes. Presented herein is an unprecedented example of vinylogous reactivity exemplified by the rhodium‐catalyzed asymmetric ring‐opening reaction of oxabicycles. This strategy also provides a powerful route to incorporate the biologically useful coumarin motif into the hydronapthalene scaffold.