Relay Iron/Chiral Brønsted Acid Catalysis: Enantioselective Hydrogenation of Benzoxazinones

An asymmetric hydrogenation reaction of benzoxazinones has been accomplished via a relay iron/chiral Brønsted acid catalysis. This approach provides a variety of chiral dihydrobenzoxazinones in good to high yields (75–96%) and enantioselectivities (up to 98:2 er). It is noteworthy that challenging 3...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2015-02, Vol.137 (7), p.2763-2768
Main Authors: Lu, Liang-Qiu, Li, Yuehui, Junge, Kathrin, Beller, Matthias
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An asymmetric hydrogenation reaction of benzoxazinones has been accomplished via a relay iron/chiral Brønsted acid catalysis. This approach provides a variety of chiral dihydrobenzoxazinones in good to high yields (75–96%) and enantioselectivities (up to 98:2 er). It is noteworthy that challenging 3-alkyl-substituted substrates underwent highly enantioselective reduction. A key to success is the utilization of a nonchiral phosphine ligand to reduce disadvantageous background reactions through tuning the catalytic activity of Fe3(CO)12.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b00085