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Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans

Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans
Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans
Combining the desymmetrization of a prochiral bis-hydroxymethyl group with the epimerization of a chiral furanyl ether in a single transformation, high levels of double diastereoselectivity have been achieved in a synthesis of 2,4,5-trisubstituted tetrahydropyrans, which proceeds under thermodynamic control.
0022-3263
3441-3455
Cooper, Dennis A.
46c3b0de-0b38-4061-b728-7a6c9d95b8be
Robbins, Emma
9e332abe-26f4-4131-8592-25140380d4bd
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
O’brien, Matthew
58536862-e94e-4e15-8b1c-02ac3c62cb01
Cooper, Dennis A.
46c3b0de-0b38-4061-b728-7a6c9d95b8be
Robbins, Emma
9e332abe-26f4-4131-8592-25140380d4bd
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
O’brien, Matthew
58536862-e94e-4e15-8b1c-02ac3c62cb01

Cooper, Dennis A., Robbins, Emma, Tizzard, Graham J., Coles, Simon J. and O’brien, Matthew (2017) Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans. The Journal of Organic Chemistry, 82 (7), 3441-3455. (doi:10.1021/acs.joc.6b02831).

Record type: Article

Abstract

Combining the desymmetrization of a prochiral bis-hydroxymethyl group with the epimerization of a chiral furanyl ether in a single transformation, high levels of double diastereoselectivity have been achieved in a synthesis of 2,4,5-trisubstituted tetrahydropyrans, which proceeds under thermodynamic control.

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ACCEPTED_JOC_THP_PAPER - Accepted Manuscript
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e-pub ahead of print date: 28 February 2017
Published date: 7 April 2017
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Organisations: Chemistry Research Support

Identifiers

Local EPrints ID: 410892
URI: http://eprints.soton.ac.uk/id/eprint/410892
DOI: doi:10.1021/acs.joc.6b02831
ISSN: 0022-3263
PURE UUID: 6d23ee78-156c-4f50-a9e8-2004fac08c66
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 09 Jun 2017 16:31
Last modified: 16 Mar 2024 05:25

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Contributors

Author: Dennis A. Cooper
Author: Emma Robbins
Author: Graham J. Tizzard ORCID iD
Author: Simon J. Coles ORCID iD
Author: Matthew O’brien

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