title: Kinetic resolution of racemic 2-hydroxy-γ-butyrolactones by asymmetric esterification using diphenylacetic acid with pivalic anhydride and a chiral acyl-transfer catalyst.
abstract: Various optically active 2-hydroxy-γ-butyrolactone derivatives are produced via the kinetic resolution of racemic 2-hydroxy-γ-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.
authors: Department of Chemistry, Graduate School of Science and Engineering, Shimane University, 1060 Nishikawatsu-cho, Matsue, Shimane 690-8504, Japan.
authors: Kenya
authors: K
authors: Nakata
authors: Kouya
authors: K
authors: Gotoh
authors: Keisuke
authors: K
authors: Ono
authors: Kengo
authors: K
authors: Futami
authors: Isamu
authors: I
authors: Shiina