Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones

Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones

We disclose the first catalytic activation of carbohydrates as formaldehyde equivalents to generate acyl anions as one-carbon nucleophilic units for a Stetter reaction. The activation involves N-heterocyclic carbene (NHC)-catalyzed C–C bond cleavage of carbohydrates via a retro-benzoin-type process...

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Main Authors: Zhang, Junmin, Xing, Chong, Tiwari, Bhoopendra, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
DRNTU::Science::Chemistry
Online Access:https://hdl.handle.net/10356/104155
http://hdl.handle.net/10220/19437
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1041552020-03-07T12:34:57Z Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones Zhang, Junmin Xing, Chong Tiwari, Bhoopendra Chi, Robin Yonggui School of Physical and Mathematical Sciences DRNTU::Science::Chemistry We disclose the first catalytic activation of carbohydrates as formaldehyde equivalents to generate acyl anions as one-carbon nucleophilic units for a Stetter reaction. The activation involves N-heterocyclic carbene (NHC)-catalyzed C–C bond cleavage of carbohydrates via a retro-benzoin-type process to generate the acyl anion intermediates. This Stetter reaction constitutes the first success in generating formal formaldehyde-derived acyl anions as one-carbon nucleophiles for non-self-benzoin processes. The renewable nature of carbohydrates, accessible from biomass, further highlights the practical potential of this fundamentally interesting catalytic activation. 2014-05-26T01:23:58Z 2019-12-06T21:27:35Z 2014-05-26T01:23:58Z 2019-12-06T21:27:35Z 2013 2013 Journal Article Zhang, J., Xing, C., Tiwari, B., & Chi, Y. R. (2013). Catalytic Activation of Carbohydrates as Formaldehyde Equivalents for Stetter Reaction with Enones. Journal of the American Chemical Society, 135(22), 8113–8116. 0002-7863 https://hdl.handle.net/10356/104155 http://hdl.handle.net/10220/19437 10.1021/ja401511r 173634 en Journal of the American Chemical Society © 2013 American Chemical Society.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry
spellingShingle DRNTU::Science::Chemistry
Zhang, Junmin
Xing, Chong
Tiwari, Bhoopendra
Chi, Robin Yonggui
Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones
description We disclose the first catalytic activation of carbohydrates as formaldehyde equivalents to generate acyl anions as one-carbon nucleophilic units for a Stetter reaction. The activation involves N-heterocyclic carbene (NHC)-catalyzed C–C bond cleavage of carbohydrates via a retro-benzoin-type process to generate the acyl anion intermediates. This Stetter reaction constitutes the first success in generating formal formaldehyde-derived acyl anions as one-carbon nucleophiles for non-self-benzoin processes. The renewable nature of carbohydrates, accessible from biomass, further highlights the practical potential of this fundamentally interesting catalytic activation.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Zhang, Junmin
Xing, Chong
Tiwari, Bhoopendra
Chi, Robin Yonggui
format Article
author Zhang, Junmin
Xing, Chong
Tiwari, Bhoopendra
Chi, Robin Yonggui
author_sort Zhang, Junmin
title Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones
title_short Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones
title_full Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones
title_fullStr Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones
title_full_unstemmed Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones
title_sort catalytic activation of carbohydrates as formaldehyde equivalents for stetter reaction with enones
publishDate 2014
url https://hdl.handle.net/10356/104155
http://hdl.handle.net/10220/19437
_version_ 1681039181872103424

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