Mild and General Zinc-Alkoxide-Catalyzed Allylations of Ketones with Allyl Pinacol Boronates
摘要:
A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.
Allylation and Crotylation of Ketones and Aldehydes Using Potassium Organotrifluoroborate Salts under Lewis Acid and Montmorillonite K10 Catalyzed Conditions
作者:Farhad Nowrouzi、Avinash N. Thadani、Robert A. Batey
DOI:10.1021/ol900599q
日期:2009.6.18
Two convenient highly diastereoselective protocols for the allylation and crotylation of ketones using practical, air- and water-stable potassium allyl and crotyltrifluoroborate salts have been developed. BF3·OEt2 and montmorillonite clay are used as catalysts to promoteadditions. The montmorillonite-catalyzed method in particular is very robust, providing a straightforward and scalable method for
Mild and General Zinc-Alkoxide-Catalyzed Allylations of Ketones with Allyl Pinacol Boronates
作者:Keith R. Fandrick、Daniel R. Fandrick、Joe J. Gao、Jonathan T. Reeves、Zhulin Tan、Wenjie Li、Jinhua J. Song、Bruce Lu、Nathan K. Yee、Chris H. Senanayake
DOI:10.1021/ol101301s
日期:2010.9.3
A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.