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Ion-tagged prolinamide organocatalysts for the direct aldol reaction on-water

journal contribution
posted on 2016-01-01, 00:00 authored by Daniel Eyckens, Hannah Brozinski, Joshua Delaney, Linden Servinis, Sahar Naghashian, Luke HendersonLuke Henderson
A concise synthesis of two imidazolium ion-tagged prolinamide organocatalysts 3 and 4, varying in anionic component (CF3COO- and PF6 -, respectively) is presented. The latter could be classified as an ionic liquid with a melting point of 66.3 °C, and glass transition temperature of 14.5 °C. The efficiency of each catalyst was compared via a direct aldol reaction revealing a large contrast in catalytic performance, with the catalyst bearing the PF6 - anion being superior. The optimal conditions were determined to be an on-water reaction system, and substrate scoping gave a range of desired aldol products in high conversion (up to >99 %), dr (up to 98:2), and er (up to 96:4). The application of these catalysts to beta-nitrostyrene conjugate addition is also presented. Graphical Abstract: [Figure not available: see fulltext.]

History

Journal

Catalysis letters

Volume

146

Issue

1

Pagination

212 - 219

Publisher

Springer

Location

Berlin, Germany

ISSN

1011-372X

eISSN

1572-879X

Language

eng

Publication classification

C Journal article; C1 Refereed article in a scholarly journal

Copyright notice

2016, Springer