Alcohol Dehydrogenase Triggered Oxa‐Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans

Eastman, Harry, Ryan, James, Caprio, Vittorio ORCID: https://orcid.org/0000-0002-9752-6513, Maciá, Beatriz and O'Reilly, Elaine (2019) Alcohol Dehydrogenase Triggered Oxa‐Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans. ChemCatChem, 11 (16). pp. 3760-3762. ISSN 1867-3880

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Abstract

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.

Item Type:	Article
Peer-reviewed:	Yes
Date Deposited:	06 Jun 2019 08:47
Publisher:	Wiley
Additional Information:	This is an Author Accepted Manuscript of an article in ChemCatChem published by Wiley.
Divisions:	Faculties > Science and Engineering
Subject terms:	Organic Chemistry
URI:	https://e-space.mmu.ac.uk/id/eprint/623050
DOI:	https://doi.org/10.1002/cctc.201900658
ISSN	1867-3880
e-ISSN	1867-3899

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