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One-Pot Biocatalytic Cascade Reduction of Cyclic Enimines for the Preparation of Diastereomerically Enriched N-Heterocycles
- Thomas W. ThorpeThomas W. ThorpeManchester Institute of Biotechnology, School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.More by Thomas W. Thorpe
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- Scott P. FranceScott P. FranceManchester Institute of Biotechnology, School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.Pfizer Worldwide Research and Development, 445 Eastern Point Road, Groton, Connecticut 06340, United StatesMore by Scott P. France
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- Shahed HussainShahed HussainManchester Institute of Biotechnology, School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.More by Shahed Hussain
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- James R. MarshallJames R. MarshallManchester Institute of Biotechnology, School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.More by James R. Marshall
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- Wojciech ZawodnyWojciech ZawodnyManchester Institute of Biotechnology, School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.More by Wojciech Zawodny
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- Juan Mangas-SanchezJuan Mangas-SanchezManchester Institute of Biotechnology, School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.More by Juan Mangas-Sanchez
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- Sarah L. MontgomerySarah L. MontgomeryManchester Institute of Biotechnology, School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.More by Sarah L. Montgomery
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- Roger M. HowardRoger M. HowardPfizer Worldwide Research and Development, 445 Eastern Point Road, Groton, Connecticut 06340, United StatesMore by Roger M. Howard
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- David S. B. DanielsDavid S. B. DanielsPfizer Worldwide Research and Development Discovery Park, Sandwich, Kent CT13 9NJ, U.K.More by David S. B. Daniels
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- Rajesh KumarRajesh KumarPfizer Worldwide Research and Development, 445 Eastern Point Road, Groton, Connecticut 06340, United StatesMore by Rajesh Kumar
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- Fabio Parmeggiani*Fabio Parmeggiani*[email protected]Manchester Institute of Biotechnology, School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.More by Fabio Parmeggiani
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- Nicholas J. Turner*Nicholas J. Turner*[email protected]Manchester Institute of Biotechnology, School of Chemistry, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.More by Nicholas J. Turner
Abstract
Ene-reductases (EREDs) catalyze the reduction of electron-deficient C═C bonds. Herein, we report the first example of ERED-catalyzed net reduction of C═C bonds of enimines (α,β-unsaturated imines). Preliminary studies suggest their hydrolyzed ring-open ω-amino enones are the likely substrates for this step. When combined with imine reductase (IRED)-mediated C═N reduction, the result is an efficient telescoped sequence for the preparation of diastereomerically enriched 2-substituted saturated amine heterocycles.
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