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- Title
Asymmetric Synthesis of Enantioenriched 2‐Aryl‐2,3‐Dihydrobenzofurans by a Lewis Acid Catalyzed Cyclopropanation/Intramolecular Rearrangement Sequence.
- Authors
Pandit, Rameshwar Prasad; Kim, Seung Tae; Ryu, Do Hyun
- Abstract
A cyclopropanation/intramolecular rearrangement initiated by the Michael addition of in situ generated ortho‐quinone methides (o‐QMs) has been developed for the enantioselective synthesis of 2‐aryl‐2,3‐dihydrobenzofurans containing two consecutive stereogenic centers, including a quaternary carbon atom. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in excellent yields (up to 95 %) with excellent stereoselectivity (up to >99 ee, up to >20:1 d.r.).
- Subjects
ASYMMETRIC synthesis; CYCLOPROPANATION; LEWIS acids; INTRAMOLECULAR catalysis; LEWIS acidity; STEREOSELECTIVE reactions; QUINONE; ATOMS
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 38, p13561
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201906954