Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction | Zendy

Megan L. Lanier | Zendy; Amanda C. Kasper | Zendy; Hyoungsu Kim | Zendy; Jiyong Hong | Zendy

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Synthesis of α,α′-trans-Oxepanes through an Organocatalytic Oxa-conjugate Addition Reaction

Author(s) -

Megan L. Lanier,

Amanda C. Kasper,

Hyoungsu Kim,

Jiyong Hong

Publication year - 2014

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/ol500773w

Subject(s) - chemistry , conjugate , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , mathematics , mathematical analysis

Oxepanes are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. Organocatalytic oxa-conjugate addition reactions promoted by the gem-disubstituent (Thorpe-Ingold) effect stereoselectively provided α,α'-trans-oxepanes. In addition, the potential of an organocatalytic tandem oxa-conjugate addition/α-oxidation was demonstrated in a rapid generation of molecular complexity. These organocatalytic oxa-conjugate addition reactions would provide powerful tools for the synthesis of natural products that contain highly functionalized oxepanes.

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