Kinetic Resolution of Racemic 2-Hydroxy-纬-butyrolactones by Asymmetric Esterification Using Diphenylacetic Acid with Pivalic Anhydride and a Chiral Acyl-Transfer Catalyst

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• 作者：Kenya Nakata ; Kouya Gotoh ; Keisuke Ono ; Kengo Futami ; Isamu Shiina
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：March 15, 2013
• 年：2013
• 卷：15
• 期：6
• 页码：1170-1173
• 全文大小：291K
• 年卷期：v.15,no.6(March 15, 2013)
• ISSN：1523-7052

文摘

Various optically active 2-hydroxy-纬-butyrolactone derivatives are produced via the kinetic resolution of racemic 2-hydroxy-纬-butyrolactones with diphenylacetic acid using pivalic anhydride and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst. Importantly, the substrate scope of this novel protocol is fairly broad (12 examples, s-value; up to over 1000). In addition, we succeeded in disclosing the reaction mechanism to afford high enantioselectivity using theoretical calculations and expounded on the substituent effects at the C-3 positions in 2-hydroxylactones.