Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans

Kevin Kasten; David Bradford Cordes; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1002/ejoc.201600583

Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans

Kevin Kasten, David Bradford Cordes, Alexandra Martha Zoya Slawin, Andrew David Smith

Research output: Contribution to journal › Article › peer-review

Abstract

The cinchona alkaloid-catalysed enantioselective formal [4+2] cycloaddition of ethyl 2,3-butadienoate with a range of 1,1,1-trifluoro- and 4,4,4-trifluorobutenones is investigated for the preparation of stereodefined 6- and 4-trifluoromethyl-substituted dihydropyrans. Quinidine proved to be the optimal catalyst, generating the desired products in up to 98 % ee and 81 % yield. Stereo- and chemoselective derivatization of the dihydropyrans through hydrogenation is explored.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	21
Early online date	23 Jun 2016
DOIs	https://doi.org/10.1002/ejoc.201600583
Publication status	Published - Jul 2016

Keywords

Organocatalysis
Enantioselective catalysis
Oxygen heterocycles

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10.1002/ejoc.201600583

Smith_2016_EJOC_Quinidine_AcceptedManuscript
Copyright © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1002/ejoc.201600583
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Cite this

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title = "Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans",

abstract = "The cinchona alkaloid-catalysed enantioselective formal [4+2] cycloaddition of ethyl 2,3-butadienoate with a range of 1,1,1-trifluoro- and 4,4,4-trifluorobutenones is investigated for the preparation of stereodefined 6- and 4-trifluoromethyl-substituted dihydropyrans. Quinidine proved to be the optimal catalyst, generating the desired products in up to 98 % ee and 81 % yield. Stereo- and chemoselective derivatization of the dihydropyrans through hydrogenation is explored.",

keywords = "Organocatalysis, Enantioselective catalysis, Oxygen heterocycles",

author = "Kevin Kasten and Cordes, {David Bradford} and Slawin, {Alexandra Martha Zoya} and Smith, {Andrew David}",

note = "The authors thank the Royal Society for a University Research Fellowship (ADS) and the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013), ERC Grant Agreement No. 279850 (KK), the authors also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.",

year = "2016",

month = jul,

doi = "10.1002/ejoc.201600583",

language = "English",

volume = "2016",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "21",

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T1 - Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans

AU - Kasten, Kevin

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

N1 - The authors thank the Royal Society for a University Research Fellowship (ADS) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013), ERC Grant Agreement No. 279850 (KK), the authors also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.

PY - 2016/7

Y1 - 2016/7

N2 - The cinchona alkaloid-catalysed enantioselective formal [4+2] cycloaddition of ethyl 2,3-butadienoate with a range of 1,1,1-trifluoro- and 4,4,4-trifluorobutenones is investigated for the preparation of stereodefined 6- and 4-trifluoromethyl-substituted dihydropyrans. Quinidine proved to be the optimal catalyst, generating the desired products in up to 98 % ee and 81 % yield. Stereo- and chemoselective derivatization of the dihydropyrans through hydrogenation is explored.

AB - The cinchona alkaloid-catalysed enantioselective formal [4+2] cycloaddition of ethyl 2,3-butadienoate with a range of 1,1,1-trifluoro- and 4,4,4-trifluorobutenones is investigated for the preparation of stereodefined 6- and 4-trifluoromethyl-substituted dihydropyrans. Quinidine proved to be the optimal catalyst, generating the desired products in up to 98 % ee and 81 % yield. Stereo- and chemoselective derivatization of the dihydropyrans through hydrogenation is explored.

KW - Organocatalysis

KW - Enantioselective catalysis

KW - Oxygen heterocycles

UR - http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600583/full#footer-support-info

U2 - 10.1002/ejoc.201600583

DO - 10.1002/ejoc.201600583

M3 - Article

SN - 1434-193X

VL - 2016

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 21

ER -

Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans

Abstract

Keywords

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ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis