Influence of Various Promoters on the Diastereoselectivity of Samarium(II) Iodide Mediated Reductive Carbocyclizations of ω-Iodo-α,β-unsaturated Esters Prepared from 2-Deoxy-d-ribose

✍ Scribed by Bita Samim Firouz Salari; Raphinos Kouya Biboutou; Sharon M Bennett

• Book ID: 104202884
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 319 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00583-4

✦ Synopsis

Iodo-a,b-unsaturated esters were reduced with SmI 2 or Bu 3 SnH under different conditions to give carbocyclic compounds in good yield. The stereoselectivity of the SmI 2 cyclizations varies with the choice of promoter, the reaction temperature, the identity of the hydroxyl protecting groups and the geometry of the double bond.