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Synthesis and applications to catalysis of novel cyclopentadienone iron tricarbonyl complexes

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Del Grosso, Alessandro, Chamberlain, Alexander E., Clarkson, Guy J. and Wills, Martin (2018) Synthesis and applications to catalysis of novel cyclopentadienone iron tricarbonyl complexes. Dalton Transactions, 47 (5). 1451-1470 . doi:10.1039/C7DT03250A ISSN 1477-9226.

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Official URL: https://doi.org/10.1039/C7DT03250A

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Abstract

A series of cyclopentadienone iron tricarbonyl complexes with diverse structures were prepared, in each case using the intramolecular cyclisation of a diyne as a key step. The complexes were generated as enantiomerically enriched through i) asymmetric synthesis of a C2-symmetric diol following a reported protocol, ii) resolution of enantiomerically-enriched diastereoisomers formed from a chiral alcohol and iii) kinetic resolution of a racemic ketone-containing iron tricarbonyl complex. The approaches underline the diversity of the synthetic routes which can be employed in the synthesis of homochiral cyclopentadienone iron tricarbonyl complexes. Although the complexes proved to be effective as catalysts for the reduction of ketones, the alcohol products were formed in low ees (not exceeding ca. 35%), highlighting the challenging nature of asymmetric catalysis using complexes of this type.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH): Cyclopentadiene , Ketones , Catalysis , Hydrogenation
Journal or Publication Title: Dalton Transactions
Publisher: Royal Society of Chemistry
ISSN: 1477-9226
Official Date: 7 February 2018
Dates:
DateEvent
7 February 2018Published
5 January 2018Available
8 November 2017Accepted
Volume: 47
Number: 5
Page Range: 1451-1470
DOI: 10.1039/C7DT03250A
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Open Access (Creative Commons)
Date of first compliant deposit: 14 November 2017
Date of first compliant Open Access: 15 January 2018
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
EP/M006670/1Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
UNSPECIFIEDEuropean Regional Development Fundhttp://dx.doi.org/10.13039/501100008530
UNSPECIFIEDUniversity of Warwickhttp://dx.doi.org/10.13039/501100000741
UNSPECIFIEDAdvantage West Midlands (AWM)UNSPECIFIED

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