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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.