Journal
TETRAHEDRON
Volume 68, Issue 26, Pages 5172-5178Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.03.118
Keywords
Asymmetric catalysis; Hydrogenation; Chiral spiro ligands; alpha-Arylcinnamic acids; (S)-Equol
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Funding
- National Natural Science Foundation of China
- National Basic Research Program of China [2012CB821600]
- Ministry of Education of China [B06005]
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By using iridium catalyst based on chiral spiro phosphine-oxazoline ligands, the hydrogenation of alpha-arylcinnamic acids was accomplished under ambient pressure and low catalyst loading (as low as 0.01 mol %), providing useful 2,3-diarylpropionic acids in high yields with excellent enantioselectivities (up to 99% ee). A catalytic enantioselective synthesis of (S)-equol with the present hydrogenation reaction as a key step was accomplished starting from commercially available starting materials in six steps with 48.4% overall yield. (C) 2012 Elsevier Ltd. All rights reserved.
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