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

Authors :
Quan M
Butt N
Shen J
Shen K
Liu D
Zhang W
Source :
Organic & biomolecular chemistry [Org Biomol Chem] 2013 Nov 14; Vol. 11 (42), pp. 7412-9.
Publication Year :
2013

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.

Details

Language :
English
ISSN :
1477-0539
Volume :
11
Issue :
42
Database :
MEDLINE
Journal :
Organic & biomolecular chemistry
Publication Type :
Academic Journal
Accession number :
24077558
Full Text :
https://doi.org/10.1039/c3ob41642a