Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes Catalyzed by a Brønsted Acid in Hexafluoroisopropanol | Zendy

Edward Richmond | Zendy; Vuk D. Vuković | Zendy; Joseph Moran | Zendy

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Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes Catalyzed by a Brønsted Acid in Hexafluoroisopropanol

Author(s) -

Edward Richmond,

Vuk D. Vuković,

Joseph Moran

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b03688

Subject(s) - chemistry , cyclopropane , nucleophile , ring (chemistry) , catalysis , acceptor , brønsted–lowry acid–base theory , aryl , alcohol , solvent , medicinal chemistry , electron acceptor , combinatorial chemistry , organic chemistry , physics , alkyl , condensed matter physics

A general, Brønsted acid catalyzed method for the room temperature, nucleophilic ring opening of donor-acceptor cyclopropanes in fluorinated alcohol solvent, HFIP, is described. Salient features of this method include an expanded cyclopropane scope, including those bearing single keto-acceptor groups and those bearing electron-deficient aryl groups. Notably, the catalytic system proved amenable to a wide range of nucleophiles including arenes, indoles, azides, diketones, and alcohols.

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