N-heterocyclic carbene-catalyzed δ-carbon LUMO activation of unsaturated aldehydes

N-heterocyclic carbene-catalyzed δ-carbon LUMO activation of unsaturated aldehydes

An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a δ-LUMO activation of α,β–γ,δ-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner,...

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Main Authors: Zhu, Tingshun, Mou, Chengli, Li, Baosheng, Smetankova, Marie, Song, Bao-An, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2018
Subjects:
Aldehydes
Carbon
Online Access:https://hdl.handle.net/10356/86653
http://hdl.handle.net/10220/45178
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-866532023-02-28T19:23:39Z N-heterocyclic carbene-catalyzed δ-carbon LUMO activation of unsaturated aldehydes Zhu, Tingshun Mou, Chengli Li, Baosheng Smetankova, Marie Song, Bao-An Chi, Robin Yonggui School of Physical and Mathematical Sciences Aldehydes Carbon An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a δ-LUMO activation of α,β–γ,δ-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner, were obtained via different catalytic pathways due to a simple change of the substrate. The activation of the remote δ-carbon of unsaturated aldehydes expands the synthetic potentials of NHC organocatalysis. MOE (Min. of Education, S’pore) Accepted version 2018-07-23T06:56:31Z 2019-12-06T16:26:39Z 2018-07-23T06:56:31Z 2019-12-06T16:26:39Z 2015 Journal Article Zhu, T., Mou, C., Li, B., Smetankova, M., Song, B.-A., & Chi, R. Y. (2015). N-heterocyclic carbene-catalyzed δ-carbon LUMO activation of unsaturated aldehydes. Journal of the American Chemical Society, 137(17), 5658-5661. 0002-7863 https://hdl.handle.net/10356/86653 http://hdl.handle.net/10220/45178 10.1021/jacs.5b02219 en Journal of the American Chemical Society © 2015 American Chemical Society.This is the author created version of a work that has been peer reviewed and accepted for publication by Journal of the American Chemical Society, American Chemical Society. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1021/jacs.5b02219]. 5 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Aldehydes
Carbon
spellingShingle Aldehydes
Carbon
Zhu, Tingshun
Mou, Chengli
Li, Baosheng
Smetankova, Marie
Song, Bao-An
Chi, Robin Yonggui
N-heterocyclic carbene-catalyzed δ-carbon LUMO activation of unsaturated aldehydes
description An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a δ-LUMO activation of α,β–γ,δ-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner, were obtained via different catalytic pathways due to a simple change of the substrate. The activation of the remote δ-carbon of unsaturated aldehydes expands the synthetic potentials of NHC organocatalysis.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Zhu, Tingshun
Mou, Chengli
Li, Baosheng
Smetankova, Marie
Song, Bao-An
Chi, Robin Yonggui
format Article
author Zhu, Tingshun
Mou, Chengli
Li, Baosheng
Smetankova, Marie
Song, Bao-An
Chi, Robin Yonggui
author_sort Zhu, Tingshun
title N-heterocyclic carbene-catalyzed δ-carbon LUMO activation of unsaturated aldehydes
title_short N-heterocyclic carbene-catalyzed δ-carbon LUMO activation of unsaturated aldehydes
title_full N-heterocyclic carbene-catalyzed δ-carbon LUMO activation of unsaturated aldehydes
title_fullStr N-heterocyclic carbene-catalyzed δ-carbon LUMO activation of unsaturated aldehydes
title_full_unstemmed N-heterocyclic carbene-catalyzed δ-carbon LUMO activation of unsaturated aldehydes
title_sort n-heterocyclic carbene-catalyzed δ-carbon lumo activation of unsaturated aldehydes
publishDate 2018
url https://hdl.handle.net/10356/86653
http://hdl.handle.net/10220/45178
_version_ 1759856767343263744

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