Revisiting the Cleavage of Evans Oxazolidinones with
LiOH/H2O2
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Version 1 2019-06-16, 12:03Version 1 2019-06-16, 12:03
Posted on 2019-06-16 - 12:03
The use of LiOH/H2O2 for cleavage of Evans
oxazolidinones is an essential but often overlooked part of using
these ubiquitous chiral auxiliaries in synthetic routes. These conditions
were disclosed in the literature more than 30 years ago and have found
widespread use with little change. During studies focused on the synthesis
of a drug candidate, we discovered the evolution of oxygen under the
LiOH/H2O2 conditions for cleavage of an Evans
auxiliary. We find this phenomenon to be general and tied to the fact
that the initially formed peracid is not stable under the reaction
conditions. The peracid is rapidly reduced by the excess H2O2 present in the reaction mixture, leading to the release
of a stoichiometric amount of oxygen. This can present a significant
risk for maintaining proper inertion in the presence of the flammable
organic solvent, and we propose options for safely executing this
chemistry at multikilogram scale.
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Beutner, Gregory L.; Cohen, Benjamin M.; DelMonte, Albert J.; Dixon, Darryl D.; Fraunhoffer, Kenneth J.; Glace, Andrew W.; et al. (2019). Revisiting the Cleavage of Evans Oxazolidinones with
LiOH/H2O2. ACS Publications. Collection. https://doi.org/10.1021/acs.oprd.9b00124