Cu-Catalyzed Cope-Type Hydroamination of Non-activated Olefins toward Cyclic Nitrones: Scope, Mechanism and Enantioselective Process Development.
CHEMISTRY-A EUROPEAN JOURNAL(2019)
Abstract
The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper-catalyzed Cope-type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five- and six-membered cyclic nitrones under mild conditions. In this study, heterocycle-tethered oximes were employed in the Cope-type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon-tethered gamma,delta-vinyl oximes to afford enantioenriched five-membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.
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Key words
copper,enantioselectivity,hydroamination,nitrones,oximes,reaction mechanisms
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