Asymmetric Synthesis of Enantioenriched 2‐Aryl‐2,3‐Dihydrobenzofurans by a Lewis Acid Catalyzed Cyclopropanation/Intramolecular Rearrangement Sequence | Zendy

Pandit Rameshwar Prasad | Zendy; Kim Seung Tae | Zendy; Ryu Do Hyun | Zendy

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Asymmetric Synthesis of Enantioenriched 2‐Aryl‐2,3‐Dihydrobenzofurans by a Lewis Acid Catalyzed Cyclopropanation/Intramolecular Rearrangement Sequence

Author(s) -

Pandit Rameshwar Prasad,

Kim Seung Tae,

Ryu Do Hyun

Publication year - 2019

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201906954

Subject(s) - cyclopropanation , stereocenter , enantioselective synthesis , intramolecular force , chemistry , lewis acids and bases , aryl , stereoselectivity , stereochemistry , catalysis , medicinal chemistry , organic chemistry , alkyl

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.).

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