Chemical Communications

Samarium (II) iodide-mediated intramolecular pinacol coupling reactions with cyclopropyl ketones

SL Foster, S Handa, M Krafft, D Rowling

Index: Foster, Sarah L.; Handa, Sandeep; Krafft, Michael; Rowling, David Chemical Communications, 2007 , # 45 p. 4791 - 4793

Full Text: HTML

Citation Number: 6

Abstract

One particularly common transformation mediated by SmI 2 is the pinacol coupling reaction of carbonyls to produce 1,2-diols. 6 The intramolecular reaction has been widely employed for the synthesis of carbocyclic systems, 2,7 and we have reported its use to access N-heterocyclic diols . 8 The typical mechanisms that have been proposed for low-valent metal-mediated pinacol reactions are shown in Scheme 1. 6,9 Initial formation of an anionic ketyl radical can be ...