Size‐Exclusion Borane‐Catalyzed Domino 1,3‐Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3‐Allylic Shift Aptitude | Zendy

Fegyverneki Dániel | Zendy; Kolozsvári Natália | Zendy; Molnár Dániel | Zendy; Egyed Orsolya | Zendy; Holczbauer Tamás | Zendy; Soós Tibor | Zendy

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Size‐Exclusion Borane‐Catalyzed Domino 1,3‐Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3‐Allylic Shift Aptitude

Author(s) -

Fegyverneki Dániel,

Kolozsvári Natália,

Molnár Dániel,

Egyed Orsolya,

Holczbauer Tamás,

Soós Tibor

Publication year - 2019

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201805208

Subject(s) - borane , allylic rearrangement , claisen rearrangement , catalysis , chemistry , hydrosilylation , valence (chemistry) , domino , medicinal chemistry , organic chemistry

The reductive Ireland–Claisen rearrangement through borane‐mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3‐allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.

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