Alcohol Dehydrogenase?triggered Oxa?Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans

Eastman, Harry; Ryan, James; Maci�, Beatriz; Caprio, Vittorio; O'Reilly, Elaine

Abstract

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim An alcohol dehydrogenase-mediated asymmetric reduction and subsequent intramolecular oxa-Michael reaction has been developed for the preparation of tetrahydropyrans (or oxanes) and tetrahydrofurans, in excellent conversion, yield and high enantiomeric and diastereomeric excess. To highlight the utility of the methodology, we report the synthesis of an analogue of the fungal antioxidant brocaketone A. Also described is the preparation of the (–)-(R,R)-enantiomer of the natural product, (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid.

Citation

Eastman, H., Ryan, J., Maciá, B., Caprio, V., & O'Reilly, E. (2019). Alcohol Dehydrogenase‐triggered Oxa‐Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans. ChemCatChem, 11(16), 3760-3762. https://doi.org/10.1002/cctc.201900658

• Journal Article Type: Article
• Acceptance Date: May 29, 2019
• Online Publication Date: Jul 9, 2019
• Publication Date: Jul 9, 2019
• Deposit Date: Aug 2, 2019
• Publicly Available Date: Jul 10, 2020
• Journal: ChemCatChem
• Print ISSN: 1867-3880
• Electronic ISSN: 1867-3899
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 11
• Issue: 16
• Pages: 3760-3762
• DOI: https://doi.org/10.1002/cctc.201900658
• Keywords: Physical and Theoretical Chemistry; Inorganic Chemistry; Organic Chemistry; Catalysis
• Public URL: https://nottingham-repository.worktribe.com/output/2382105
• Publisher URL: https://onlinelibrary.wiley.com/doi/full/10.1002/cctc.201900658
• Additional Information: This is the peer reviewed version of the following article: Eastman, H. , Ryan, J. , Maciá, B. , Caprio, V. and O'Reilly, E. (2019), Alcohol Dehydrogenase‐triggered Oxa‐Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans. ChemCatChem. , which has been published in final form at doi:10.1002/cctc.201900658. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.