Reductive radical cyclization of cyclic γ-cyanoketones promoted by samarium(II) iodide without photoirradiation

✍ Scribed by Kiyomi Kakiuchi; Yasunari Fujioka; Hirohisa Yamamura; Ken Tsutsumi; Tsumoru Morimoto; Hideo Kurosawa

• Book ID: 104231628
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 69 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01579-9

✦ Synopsis

Reaction of cyclic g-cyanoketones with 3 equiv. of SmI 2 in the presence of t-BuOH as a proton source in HMPA-THF without photoirradiation gave the desired a-hydroxycycloalkanones along with overreduced ketones after hydrolysis. In the absence of t-BuOH, the formation of the overreduced ketones was depressed and the yields of the a-hydroxyketones increased, while the reaction proceeded slowly.