对β，γ-不饱和α-酮酯的高度立体选择性氧-迈克尔加成反应：3-羟基丁烯内酯的快速对映选择性合成。
Highly stereoselective oxy-michael additions to beta,gamma-unsaturated alpha-keto esters: rapid enantioselective synthesis of 3-hydroxybutenolides.
作者信息
Xiong Xin, Ovens Caroline, Pilling Adam W, Ward John W, Dixon Darren J
机构信息
School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK.
出版信息
Org Lett. 2008 Feb 21;10(4):565-7. doi: 10.1021/ol702693m. Epub 2008 Jan 23.
PMID:18211073
Abstract
The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl delta-lactol to gamma-substituted beta,gamma-unsaturated alpha-keto esters leading to the direct formation of THP*-protected gamma-hydroxy alpha-keto ester derivatives is described. Subsequent acid-mediated deprotection affords the 3-hydroxybutenolides in high yields.
摘要
描述了(6S)-甲基δ-内酯的“裸露”阴离子对γ-取代的β,γ-不饱和α-酮酯的高度非对映选择性氧-Michael加成反应，该反应直接生成THP*保护的γ-羟基α-酮酯衍生物。随后通过酸介导的脱保护反应以高收率得到3-羟基丁烯内酯。
Zotero 插件