Abstract
(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one has been synthesized for the first time by the enantiospecific oxidative carbonylation of commercially available (S)-2-amino-3-methyl-1,1-diphenylbutan-1-ol. The cyclocarbonylation reaction was carried out at 100 °C in 1,2-dimethoxyethane (DME) as the solvent for 15 h, under 20 atm of a 4:1 mixture of CO–air and in the presence of the catalytic system PdI2/KI (substrate:KI:PdI2 molar ratio = 100:10:1), to give the oxazolidinone derivative in 81% isolated yield.
Highlights
Oxazolidin-2-ones are a very important class of heterocyclic derivatives
After 15 h reaction time, the TLC analysis conversion of the substrate and the formation of a product, which was isolated by crystallization and which was by crystallization and identified as (S)-4-isopropyl-5,5-diphenyloxazolidin-2-one
2(anionic: clarity): 2of can bebe rationalized shown informed iodide for nitrogen result, considering the high steric hindrance present the palladation is giveinsertion a carbamoylpalladium palladation
Summary
Oxazolidin-2-ones are a very important class of heterocyclic derivatives. Many compounds possessing the oxazolidinone scaffold present important pharmacological activities, antimicrobial activity in particular [1]. Molbank 2018, 2018, M9xx FOR PEER REVIEW Enantiospecific synthesis of (S)-4-isopropyl-5,5-diphenyloxazolidin-2-one 2 by PdI2/KIcatalyzed oxidative carbonylation of commercially available (S)-2-amino-3-methyl-1,1Scheme 1.1. CO-air,ininconjunction the presence of catalytic amounts of15
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