Relay iron/chiral brønsted acid catalysis: Enantioselective hydrogenation of benzoxazinones

Liang Qiu Lu, Yuehui Li, Kathrin Junge, Matthias Beller

Research output: Contribution to journalArticlepeer-review

90 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)2763-2768
Number of pages6
JournalJournal of the American Chemical Society
Volume137
Issue number7
DOIs
StatePublished - 25 Feb 2015
Externally publishedYes

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