Li Hao, Yang Hao, Liebeskind Lanny S
Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
Org Lett. 2008 Oct 2;10(19):4375-8. doi: 10.1021/ol8018456. Epub 2008 Aug 30.
An efficient synthesis of high enantiopurity N-protected alpha-amino ketones is described. Complementing other studies using boronic acids and thiol esters, this Cu(I) diphenylphosphinate (CuDPP)-mediated, palladium-catalyzed coupling of alpha-amino thiol esters with aryl, heteroaryl, allyl, and alkenyl organostannanes gives N-protected alpha-amino ketones in high yields with high enantiopurity (in almost all cases) under mild and pH-neutral reaction conditions. The viability of pi-deficient heteroarylstannanes is an advantage of this reaction compared to the related boronic acid system.
本文描述了一种高效合成高对映体纯度的N-保护α-氨基酮的方法。与其他使用硼酸和硫醇酯的研究互补,这种由次磷酸二苯酯铜(CuDPP)介导、钯催化的α-氨基硫醇酯与芳基、杂芳基、烯丙基和链烯基有机锡烷的偶联反应,在温和且pH中性的反应条件下,能以高收率和高对映体纯度(几乎在所有情况下)得到N-保护的α-氨基酮。与相关的硼酸体系相比,贫π杂芳基锡烷的可行性是该反应的一个优势。