ChemInform Abstract: Intramolecular Ketone—Nitrile Reductive Coupling Reactions Promoted by Samarium(II) Iodide.

✍ Scribed by Gary A. Molander; Chad N. Wolfe

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 37 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199923053

✦ Synopsis

Intramolecular Ketone-Nitrile Reductive Coupling Reactions Promoted by Samarium(II) Iodide.

-The photochemically induced reaction of keto nitriles of type (I), (III), and (V) with SmI 2 offers an efficient route to prepare monocyclic, fused bicyclic, and bridged α-hydroxy ketones. 5-exo-Coupling proceeds with better results than 6-exo-cyclization. A sequential reaction consisting of a nucleophilic acyl substitution followed by a ketyl-nitrile coupling is also possible. -(MOLANDER, GARY A.; WOLFE, CHAD N.;