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...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2014
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/104155 http://hdl.handle.net/10220/19437 |
| _version_ | 1826117527880597504 |
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| author | Zhang, Junmin Xing, Chong Tiwari, Bhoopendra Chi, Robin Yonggui |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Zhang, Junmin Xing, Chong Tiwari, Bhoopendra Chi, Robin Yonggui |
| author_sort | Zhang, Junmin |
| collection | NTU |
| 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. |
| first_indexed | 2024-10-01T04:28:45Z |
| format | Journal Article |
| id | ntu-10356/104155 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:28:45Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-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. |
| 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 |
| title | 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_short | 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 |
| topic | DRNTU::Science::Chemistry |
| url | https://hdl.handle.net/10356/104155 http://hdl.handle.net/10220/19437 |
| work_keys_str_mv | AT zhangjunmin catalyticactivationofcarbohydratesasformaldehydeequivalentsforstetterreactionwithenones AT xingchong catalyticactivationofcarbohydratesasformaldehydeequivalentsforstetterreactionwithenones AT tiwaribhoopendra catalyticactivationofcarbohydratesasformaldehydeequivalentsforstetterreactionwithenones AT chirobinyonggui catalyticactivationofcarbohydratesasformaldehydeequivalentsforstetterreactionwithenones |