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. Issue 9 (27th December 2018)

• Record Type: Journal Article
• Authors: Fegyverneki, Dániel; Kolozsvári, Natália; Molnár, Dániel; Egyed, Orsolya; Holczbauer, Tamás; Soós, Tibor
• Is Part Of: Chemistry. Volume 25:Issue 9(2019)
• Page Start: 2179
• Page End: 2183
• Publication Date: 2018-12-27
• Subjects: boranes -- diastereoselectivity -- Ireland–Claisen -- sigmatropic rearrangement -- silanes; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201805208
• Languages: English
• ISSNs: 0947-6539

Abstract

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