Enantioselective aza-Henry reaction of t-Boc protected imines and nitroalkanes with bifunctional squaramide organocatalystsElectronic supplementary information (ESI) available. See DOI: 10.1039/c6nj04078k

An organocatalytic asymmetric aza-Henry reaction of t -Boc protected imines with nitroalkanes has been established by chiral acid-base type bifunctional Cinchona alkaloid/squaramide organocatalysts. The cooperation of a quinine motif as a base and sterically encumbered squaramide (H-bond donor) enab...

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Bibliographic Details
Main Authors Susam, Dil ad, Tanyeli, Cihangir
Format Journal Article
LanguageEnglish
Published 02.05.2017
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Summary:An organocatalytic asymmetric aza-Henry reaction of t -Boc protected imines with nitroalkanes has been established by chiral acid-base type bifunctional Cinchona alkaloid/squaramide organocatalysts. The cooperation of a quinine motif as a base and sterically encumbered squaramide (H-bond donor) enabled mostly complete conversion of a range of reactants into the corresponding aza-Henry products at room temperature with good selectivities (up to 91% ee with 10 mol% catalyst loading). A quinine-derived sterically encumbered squaramide organocatalyst afforded high enantioselectivity and excellent conversion in an aza-Henry reaction performed with imines and nitroalkanes.
Bibliography:10.1039/c6nj04078k
Electronic supplementary information (ESI) available. See DOI
ISSN:1144-0546
1369-9261
DOI:10.1039/c6nj04078k