J. Izquierdo, M. A. Pericàs
Jan 4, 2016
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Influential Citations
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Journal
ACS Catalysis
Abstract
A polystyrene-supported, enantiopure benzotetramisole (BTM) analogue (5) has been synthesized from (2S,3S)-phenylglycidol through a five-step sequence involving a copper-catalyzed alkyne azide cycloaddition (CuAAC) reaction as the final, immobilization step. The functional resin 5 (f = 0.9 mmol g–1) has been successfully used as a highly active and enantioselective catalyst in the domino Michael addition/cyclization reaction of in situ activated arylacetic acids (7) with chalcone-type tosylimines (6), leading to dihydropyridinones 8 (17 examples) to afford the products with excellent yields and very high enantioselectivity (mean ee 97.4%). The deactivation of 5 by species present during the catalytic process has been studied, and pivaloyl chloride (required for the activation of the arylacetic acid) has been identified as the main source of deactivation. A simple experimental protocol taking this fact into account has allowed the multiple recycling of 5 with only a marginal decrease in catalytic activity ...