NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides

Alyn Davies; Mark D. Greenhalgh; Alexandra M. Z. Slawin; Andrew David Smith

doi:10.3762/bjoc.16.129

NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides

Alyn Davies, Mark D. Greenhalgh, Alexandra M. Z. Slawin, Andrew David Smith

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

Abstract

The N-heterocyclic carbene (NHC) catalyzed formal [2+2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring-opening with an amine or reducing agent is described. The resulting β-hydroxy-β-trifluoromethyl amide and alcohol products are produced with reasonable diastereocontrol (typically ~70:30 dr) and excellent enantioselectivity, and can be isolated in moderate to good yield as a single diastereoisomer.

Original language	English
Pages (from-to)	1572-1578
Journal	Beilstein Journal of Organic Chemistry
Volume	16
DOIs	https://doi.org/10.3762/bjoc.16.129
Publication status	Published - 30 Jun 2020

Keywords

Trifluoromethyl group
N-heterocyclic carbene
Enantioselective catalysis
Formal [2+2]-cycloaddition
Ring-opening

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10.3762/bjoc.16.129Licence: CC BY

Davies_2020_BJOC_NHC_CC
Copyright © 2020 Davies et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
Final published version, 856 KBLicence: CC BY

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

NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides (dataset)
Smith, A. D. (Creator), Davies, A. (Creator), Slawin, A. M. Z. (Creator) & Greenhalgh, M. D. (Creator), University of St Andrews, 7 Jul 2020
DOI: 10.17630/c093507d-9801-48a6-a0b1-4c00f2c86456
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title = "NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides",

abstract = "The N-heterocyclic carbene (NHC) catalyzed formal [2+2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring-opening with an amine or reducing agent is described. The resulting β-hydroxy-β-trifluoromethyl amide and alcohol products are produced with reasonable diastereocontrol (typically ~70:30 dr) and excellent enantioselectivity, and can be isolated in moderate to good yield as a single diastereoisomer.",

keywords = "Trifluoromethyl group, N-heterocyclic carbene, Enantioselective catalysis, Formal [2+2]-cycloaddition, Ring-opening",

author = "Alyn Davies and Greenhalgh, {Mark D.} and Slawin, {Alexandra M. Z.} and Smith, {Andrew David}",

note = "Authors acknowlege the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013) ERC grant agreement no. 279850 (A.T.D.). We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.",

year = "2020",

month = jun,

day = "30",

doi = "10.3762/bjoc.16.129",

language = "English",

volume = "16",

pages = "1572--1578",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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T1 - NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides

AU - Davies, Alyn

AU - Greenhalgh, Mark D.

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew David

N1 - Authors acknowlege the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC grant agreement no. 279850 (A.T.D.). We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.

PY - 2020/6/30

Y1 - 2020/6/30

N2 - The N-heterocyclic carbene (NHC) catalyzed formal [2+2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring-opening with an amine or reducing agent is described. The resulting β-hydroxy-β-trifluoromethyl amide and alcohol products are produced with reasonable diastereocontrol (typically ~70:30 dr) and excellent enantioselectivity, and can be isolated in moderate to good yield as a single diastereoisomer.

AB - The N-heterocyclic carbene (NHC) catalyzed formal [2+2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring-opening with an amine or reducing agent is described. The resulting β-hydroxy-β-trifluoromethyl amide and alcohol products are produced with reasonable diastereocontrol (typically ~70:30 dr) and excellent enantioselectivity, and can be isolated in moderate to good yield as a single diastereoisomer.

KW - Trifluoromethyl group

KW - N-heterocyclic carbene

KW - Enantioselective catalysis

KW - Formal [2+2]-cycloaddition

KW - Ring-opening

U2 - 10.3762/bjoc.16.129

DO - 10.3762/bjoc.16.129

M3 - Article

SN - 1860-5397

VL - 16

SP - 1572

EP - 1578

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides

Abstract

Keywords

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Projects

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

Datasets

NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides (dataset)

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