Solvent-Controlled Regioselective Reaction of 2-Methyleneaziridines with Acrylic/Propargylic Acids: Synthesis of Carboxylate Aziridine/Acetone Esters

Abstract

Herein, we report a convenient solvent-controlled regioselective esterification to access two types of carboxylate esters without any additive or non-green activation strategy. In this transformation, 2-methyleneaziridines served as an ester reagent, providing two alternative electrophilic carbon centers. Notably, this protocol is suitable for some structure-complicated clinical molecules with a carboxylic acid group, presenting remarkable application potential.

α-Acyloxylation of Ketones/Cyclic Ethers Mediated by Hypervalent Iodine(III) Reagents as Oxidants and Nucleophilic Sources

“…2-Oxopropyl But-2-ynoate (3na). 20 Product 3na was synthesized according to general experimental procedure I and purified by column chromatography (15:1 petroleum ether/ethyl acetate): colorless liquid (56 mg, 0.40 mmol, 40% yield); 1 H NMR (400 MHz, CDCl 3 ) δ 4.70 (s, 2H), 2.17 (s, 3H), 2.01 (s, 3H); 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 200.7, 152.7, 87.7, 71.6, 69.0, 26.1, 3.9.…”