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Issue 42, 2013
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The synthesis of chiral β-aryl-α,β-unsaturated amino alcohols via a Pd-catalyzed asymmetric allylic amination

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Abstract

Chiral β-aryl-α,β-unsaturated amino alcohols were synthesized via a Pd-catalyzed asymmetric allylic amination of 4-aryl-1,3-dioxolan-2-one using planar chiral 1,2-disubstituted ferrocene-based phosphinooxazolines as ligands. Under the optimized reaction conditions, a series of substrates were examined and the products were obtained in good to excellent yields (up to 92%) and enantioselectivities (up to 98% ee) under mild reaction conditions. The desired products were determined to be of (R)-configuration and could subsequently be transformed into compounds with interesting biological activity using simple transformations.

Graphical abstract: The synthesis of chiral β-aryl-α,β-unsaturated amino alcohols via a Pd-catalyzed asymmetric allylic amination

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Article information


Submitted
12 Aug 2013
Accepted
08 Sep 2013
First published
30 Sep 2013

Org. Biomol. Chem., 2013,11, 7412-7419
Article type
Paper

The synthesis of chiral β-aryl-α,β-unsaturated amino alcohols via a Pd-catalyzed asymmetric allylic amination

M. Quan, N. Butt, J. Shen, K. Shen, D. Liu and W. Zhang, Org. Biomol. Chem., 2013, 11, 7412
DOI: 10.1039/C3OB41642A

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