Dynamic kinetic resolution of 2-methyl-2-nitrocyclohexanol: Combining the intramolecular nitroaldol (Henry) reaction & lipase catalysed resolution

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Dynamic kinetic resolution of 2-methyl-2-nitrocyclohexanol: Combining the intramolecular nitroaldol (Henry) reaction & lipase catalysed resolution

Foley, Aoife M.; Gavin, Declan P.; Deasy, Rebecca E.; Milner, Sinéad E.; Moody, Thomas S.; Eccles, Kevin S.; Lawrence, Simon E.; Maguire, Anita R.
Date: 2018-02-02
Copyright: © 2018, Elsevier B.V. All rights reserved. This manuscript version is made available under the CC-BY-NC-ND 4.0 license.
Copyright information: https://creativecommons.org/licenses/by-nc-nd/4.0/
Full text restriction information: Access to this article is restricted until 24 months after publication by request of the publisher.
Restriction lift date: 2020-02-02
Citation: Foley, A. M., Gavin, D. P.; Deasy, R. E., Milner, S. E., Moody, T. S., Eccles, K. S., Lawrence, S. E. and Maguire, A. R. (2018) 'Dynamic kinetic resolution of 2-methyl-2-nitrocyclohexanol: Combining the intramolecular nitroaldol (Henry) reaction & lipase catalysed resolution', Tetrahedron. doi:10.1016/j.tet.2018.01.055
Published Version: 10.1016/j.tet.2018.01.055

Abstract:

Efforts to combine the intramolecular nitroaldol reaction with lipase-catalysed resolution of the resulting nitroaldol adduct in a one-pot dynamic kinetic resolution (DKR) are described. Significant challenges were encountered in the combination of the two systems. trans-2-Methyl-2-nitrocyclohexyl acetate (±)-3b was isolated in excellent enantiopurity (>98% ee) via a sequential DKR sequence where the lipase-mediated resolution and base-mediated interconversion of 2-methyl-2-nitrocyclohexanol 2 were effected alternately, demonstrating the feasibility of this approach initially. Further work showed, for the first time, evidence that a DKR-type system is possible for 2. Reaction engineering allowed the design of a sequential one-pot reaction system which furnished the products with excellent enantioselectivity, and good diastereoselectivity.

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© 2018, Elsevier B.V. All rights reserved. This manuscript version is made available under the CC-BY-NC-ND 4.0 license. Except where otherwise noted, this item's license is described as © 2018, Elsevier B.V. All rights reserved. This manuscript version is made available under the CC-BY-NC-ND 4.0 license.
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