Experimental and Computational Study of an Unexpected Iron-Catalyzed Carboetherification by Cooperative Metal and Ligand Substrate Interaction and Proton Shuttling

Osama El-Sepelgy, Aleksandra Brzozowska, Luis Azofra Mesa, Yoon Kyung Jang, Luigi Cavallo, Magnus Rueping

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

An iron-catalyzed cycloisomerization of allenols to deoxygenated pyranose glycals has been developed. Combined experimental and computational studies show that the iron complex exhibits a dual catalytic role in that the non-innocent cyclopentadienone ligand acts as proton shuttle by initial hydrogen abstraction from the alcohol and by facilitating protonation and deprotonation events in the isomerization and demetalation steps. Molecular orbital analysis provides insight into the unexpected and selective formation of the 3,4-dihydro-2H-pyran.
Original languageEnglish (US)
Pages (from-to)14863-14867
Number of pages5
JournalAngewandte Chemie International Edition
Volume56
Issue number47
DOIs
StatePublished - Oct 24 2017

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