Kinetic Resolution of Racemic 2‐Hydroxyarylketones by Asymmetric Esterification: Investigation of the Influence of the Co‐Base on the Selectivity. Issue 2 (24th January 2020)

• Record Type: Journal Article
• Authors: Murata, Takatsugu; Futami, Kengo; Ishikawa, Ryo; Ono, Keisuke; Nakata, Kenya; Shiina, Isamu
• Is Part Of: Asian journal of organic chemistry. Volume 9:Issue 2(2020)
• Page Start: 202
• Page End: 205
• Publication Date: 2020-01-24
• Subjects: Kinetic resolution -- 2-Hydroxketones -- Organocatalysis -- Esterification -- Carboxylic anhydrides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900702
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: An efficient kinetic resolution of a variety of racemic 2‐hydroxyarylketone derivatives was developed by asymmetric esterification protocol using diphenylacetic acid, pivalic anhydride, and a catalytic amount of ( R )‐benzotetramisole (( R )‐BTM). It was revealed that employing a tertiary amine as a co‐base in this reaction is not necessary to achieve high s ‐values. All conducted reactions proceeded smoothly with good s ‐values under the optimized reaction conditions, irrespective of the steric and electronic nature of the substituents on the aromatic rings of the substrates. The most stable transition state of the reaction was determined by density functional theory (DFT) calculations. Abstract : Kinetic resolution of racemic 2‐hydroxyarylketones was achieved by asymmetric esterification using Ph2 CHCO2 H and pivalic anhydride (Piv2 O) catalyzed by ( R )‐benzotetramisole (( R )‐BTM) with good to high s ‐values (up to 160).