Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst

Diego Javier Barrios Antunez; Mark David Greenhalgh; Charlene Fallan; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1039/C6OB01326K

Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst

Diego Javier Barrios Antunez, Mark David Greenhalgh, Charlene Fallan, Alexandra Martha Zoya Slawin, Andrew David Smith

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

Abstract

The diastereo- and enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives (15 examples, up to 96:4 dr, 95:5 er) via intramolecular Michael addition has been developed using keto-enone substrates and a bifunctional tertiary amine-thiourea catalyst. This methodology was extended to include non-activated ketone pronucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.

Original language	English
Pages (from-to)	7268-7274
Number of pages	7
Journal	Organic & Biomolecular Chemistry
Volume	14
Issue number	30
Early online date	8 Jul 2016
DOIs	https://doi.org/10.1039/C6OB01326K
Publication status	Published - 14 Aug 2016

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Manuscript Final_revised
Copyright 2016 the Authors. 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/10.1039/C6OB01326K
Accepted author manuscript, 1.11 MBLicence: Unspecified

ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis
Smith, A. D. (PI)
European Commission
1/10/11 → 30/06/17
Project: Standard

Data underpinning - Enantioselective Synthesis of 2,3-Disubstituted trans-2,3-Dihydrobenzofurans Using a Brønsted Base/Thiourea Bifunctional Catalyst
Smith, A. D. (Creator), Slawin, A. M. Z. (Contributor), Barrios Antunez, D. J. (Contributor), Greenhalgh, M. D. (Contributor) & Fallan, C. (Contributor), University of St Andrews, 2016
DOI: 10.17630/e2138b18-be8d-4632-8f92-6c1391a4d058
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title = "Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Br{\o}nsted base/thiourea bifunctional catalyst",

abstract = "The diastereo- and enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives (15 examples, up to 96:4 dr, 95:5 er) via intramolecular Michael addition has been developed using keto-enone substrates and a bifunctional tertiary amine-thiourea catalyst. This methodology was extended to include non-activated ketone pronucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.",

author = "{Barrios Antunez}, {Diego Javier} and Greenhalgh, {Mark David} and Charlene Fallan and Slawin, {Alexandra Martha Zoya} and Smith, {Andrew David}",

note = "The research leading to these results (D-J.B.A.; C. F.) has received funding from the ERC under the European Union's Seventh Framework Programme (FP7/2007-2013) / ERC grant agreement n° 279850. ADS thanks the Royal Society for a Wolfson Research Merit Award. ",

year = "2016",

month = aug,

day = "14",

doi = "10.1039/C6OB01326K",

language = "English",

volume = "14",

pages = "7268--7274",

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T1 - Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst

AU - Barrios Antunez, Diego Javier

AU - Greenhalgh, Mark David

AU - Fallan, Charlene

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

N1 - The research leading to these results (D-J.B.A.; C. F.) has received funding from the ERC under the European Union's Seventh Framework Programme (FP7/2007-2013) / ERC grant agreement n° 279850. ADS thanks the Royal Society for a Wolfson Research Merit Award.

PY - 2016/8/14

Y1 - 2016/8/14

N2 - The diastereo- and enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives (15 examples, up to 96:4 dr, 95:5 er) via intramolecular Michael addition has been developed using keto-enone substrates and a bifunctional tertiary amine-thiourea catalyst. This methodology was extended to include non-activated ketone pronucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.

AB - The diastereo- and enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofuran derivatives (15 examples, up to 96:4 dr, 95:5 er) via intramolecular Michael addition has been developed using keto-enone substrates and a bifunctional tertiary amine-thiourea catalyst. This methodology was extended to include non-activated ketone pronucleophiles for the synthesis of 2,3-disubstituted indane and 3,4-disubstituted tetrahydrofuran derivatives.

U2 - 10.1039/C6OB01326K

DO - 10.1039/C6OB01326K

M3 - Article

SN - 1477-0520

VL - 14

SP - 7268

EP - 7274

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 30

ER -

Enantioselective synthesis of 2,3-disubstituted trans-2,3-dihydrobenzofurans using a Brønsted base/thiourea bifunctional catalyst

Abstract

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

Datasets

Data underpinning - Enantioselective Synthesis of 2,3-Disubstituted trans-2,3-Dihydrobenzofurans Using a Brønsted Base/Thiourea Bifunctional Catalyst

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