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

Eastman, Harry and Ryan, James and Caprio, Vittorio and Maciá, Beatriz and O'Reilly, Elaine (2019) Alcohol Dehydrogenase Triggered Oxa‐Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans. ChemCatChem. 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.

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