Issue 11, 2012

Iridium catalyzed enantioselective hydrogenation of α-alkoxy and β-alkoxy vinyl ethers

Abstract

Iridium catalyzed, enantioselective hydrogenations of functionalized, acid-sensitive vinyl ethers are reported. These reactions are mediated by the chiral N-carbene–oxazoline complex 1 that, unlike similar N,P-ligated catalysts (6 and 7), gives hydrogenation products (with enantioselectivities up to 96%) without significant acid-mediated degradation. In general, higher enantioselectivities were observed for the allylic alcohol derivatives (2) than the α-methoxycinnamate-based compounds (4).

Graphical abstract: Iridium catalyzed enantioselective hydrogenation of α-alkoxy and β-alkoxy vinyl ethers

Supplementary files

Article information

Article type
Paper
Submitted
22 Dec 2011
Accepted
05 Mar 2012
First published
13 Apr 2012

RSC Adv., 2012,2, 4728-4735

Iridium catalyzed enantioselective hydrogenation of α-alkoxy and β-alkoxy vinyl ethers

Y. Zhu and K. Burgess, RSC Adv., 2012, 2, 4728 DOI: 10.1039/C2RA01350A

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