Synthesis of Ferrocene Oxazoline N,O ligands and Their Application in Asymmetric Ethyl- and Phenylzinc Additions to Aldehydes

The Journal of Organic Chemistry
Chris NottinghamPatrick J Guiry

Abstract

The synthesis of a range of novel gem-disubstituted ferrocene-oxazoline ligands and their application in both the asymmetric ethyl- and phenylzinc additions to aldehydes is reported. These studies reveal that gem-disubstitution of i-Pr-containing ferrocene oxazoline ligands results in increased enantioselectivity compared to their unsubstituted counterparts. Utilizing zinc catalysis, these ligands provided a wide range of secondary alcohols in yields of up to 93% with ee's of up to >99%. An interesting crystal structure of a ferrocene oxide-lithium tetramer showing lithium-nitrogen coordination in the solid state is also presented.

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Citations

Feb 17, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Julia HolzRené Peters
Oct 8, 2016·Organic & Biomolecular Chemistry·Justine DesrochesJean-François Paquin
Aug 16, 2017·Chemistry : a European Journal·Gareth E Arnott

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