Regio- and stereochemically controlled formation of hydroxamic acids from indium triflate-mediated nucleophilic ring-opening reactions with acylnitroso-Diels–Alder adducts

✍ Scribed by Baiyuan Yang; Marvin J. Miller

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 298 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.12.006

✦ Synopsis

Treatment of acylnitroso-Diels-Alder [2.2.1] bicyclic adducts 2a-b with indium triflate in an alcohol solvent induces ring-opening reactions to afford monocyclic anti-1,2-, anti-1,4-, and syn-1,4-hydroxamic acids with good to excellent regio-and stereoselectivity (up to 7:86:7). Treatment of [2.2.2] bicyclic nitroso adducts 2c-d under similar reaction conditions generates only anti-1,2-and anti-1,4-hydroxamic acids with anti-1,4-product being predominant (up to 17:83).