Golec, Jonathan C, Carter, Eve M, Ward, John W 
ORCID: 0000-0001-7186-6416, Whittingham, William G, Simon, Luis, Paton, Robert S and Dixon, Darren J
(2020)
BIMP‐Catalyzed 1,3‐Prototropic Shift for the Highly Enantioselective Synthesis of Conjugated Cyclohexenones.
Angewandte Chemie International Edition, 59 (40).
pp. 17417-17422.
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Abstract
A bifunctional iminophosphorane (BIMP)‐catalysed enantioselective synthesis of α,β‐unsaturated cyclohexenones through a facially selective 1,3‐prototropic shift of β,γ‐unsaturated prochiral isomers, under mild reaction conditions and in short reaction times, on a range of structurally diverse substrates, is reported. α,β‐Unsaturated cyclohexenone products primed for downstream derivatisation were obtained in high yields (up to 99 %) and consistently high enantioselectivity (up to 99 % ee). Computational studies into the reaction mechanism and origins of enantioselectivity, including multivariate linear regression of TS energy, were carried out and the obtained data were found to be in good agreement with experimental findings.
| Item Type: | Article |
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| Uncontrolled Keywords: | bifunctional iminophosphoranes, chiral cyclohexenone, asymmetric catalysis, organocatalysis, prototropic shift |
| Depositing User: | Symplectic Admin |
| Date Deposited: | 03 Sep 2020 10:46 |
| Last Modified: | 18 Jan 2023 23:35 |
| DOI: | 10.1002/anie.202006202 |
| Open Access URL: | https://doi.org/10.1002/anie.202006202 |
| Related URLs: | |
| URI: | https://livrepository.liverpool.ac.uk/id/eprint/3099806 |
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