Asymmetric Michael addition of 5 H-oxazol-4-ones to vinyl sulfones : stereoselective synthesis of monofluorinated analogs of 2-tertiary hydroxyl-3-methyl-substituted carboxylic acidl derivatives
An asymmetric Michael addition of 5H-oxazol-4-ones to vinyl sulfones has been developed. In the presence of 10 mol % of quinine-based benzyl-substituted thiourea as catalyst at 0 °C, the products could be obtained with excellent enantio- and diastereoselectivity (up to>99 % ee and>20:1 dr). 1....
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2015
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| Online Access: | https://hdl.handle.net/10356/106585 http://hdl.handle.net/10220/25011 http://dx.doi.org/10.1002/adsc.201400649 |
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| author | Liu, Qian Qiao, Baokun Chin, Kek Foo Tan, Choon-Hong Jiang, Zhiyong |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Liu, Qian Qiao, Baokun Chin, Kek Foo Tan, Choon-Hong Jiang, Zhiyong |
| author_sort | Liu, Qian |
| collection | NTU |
| description | An asymmetric Michael addition of 5H-oxazol-4-ones to vinyl sulfones has been developed. In the presence of 10 mol % of quinine-based benzyl-substituted thiourea as catalyst at 0 °C, the products could be obtained with excellent enantio- and diastereoselectivity (up to>99 % ee and>20:1 dr). 1.0 mol % of catalyst also produced the corresponding adducts with similar stereoselective results when the temperature was increased to 25 °C. The obtained adducts have been demonstrated as significant synthetic fragments to conveniently access the monofluorinated analogs of biologically important 2-tertiary hydroxyl-3-methyl-substituted carboxylic acid derivatives. |
| first_indexed | 2024-10-01T05:41:51Z |
| format | Journal Article |
| id | ntu-10356/106585 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:41:51Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/1065852019-12-06T22:14:35Z Asymmetric Michael addition of 5 H-oxazol-4-ones to vinyl sulfones : stereoselective synthesis of monofluorinated analogs of 2-tertiary hydroxyl-3-methyl-substituted carboxylic acidl derivatives Liu, Qian Qiao, Baokun Chin, Kek Foo Tan, Choon-Hong Jiang, Zhiyong School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Physical chemistry::Catalysis An asymmetric Michael addition of 5H-oxazol-4-ones to vinyl sulfones has been developed. In the presence of 10 mol % of quinine-based benzyl-substituted thiourea as catalyst at 0 °C, the products could be obtained with excellent enantio- and diastereoselectivity (up to>99 % ee and>20:1 dr). 1.0 mol % of catalyst also produced the corresponding adducts with similar stereoselective results when the temperature was increased to 25 °C. The obtained adducts have been demonstrated as significant synthetic fragments to conveniently access the monofluorinated analogs of biologically important 2-tertiary hydroxyl-3-methyl-substituted carboxylic acid derivatives. 2015-02-02T09:01:29Z 2019-12-06T22:14:35Z 2015-02-02T09:01:29Z 2019-12-06T22:14:35Z 2014 2014 Journal Article Liu, Q., Qiao, B., Chin, K. F., Tan, C.-H., & Jiang, Z. (2014). Asymmetric Michael addition of 5 H-oxazol-4-ones to vinyl sulfones : stereoselective synthesis of monofluorinated analogs of 2-tertiary hydroxyl-3-methyl-substituted carboxylic acidl derivatives. Advanced synthesis & catalysis, 356(18), 3777-3783. 1615-4150 https://hdl.handle.net/10356/106585 http://hdl.handle.net/10220/25011 http://dx.doi.org/10.1002/adsc.201400649 en Advanced synthesis & catalysis © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Physical chemistry::Catalysis Liu, Qian Qiao, Baokun Chin, Kek Foo Tan, Choon-Hong Jiang, Zhiyong Asymmetric Michael addition of 5 H-oxazol-4-ones to vinyl sulfones : stereoselective synthesis of monofluorinated analogs of 2-tertiary hydroxyl-3-methyl-substituted carboxylic acidl derivatives |
| title | Asymmetric Michael addition of 5 H-oxazol-4-ones to vinyl sulfones : stereoselective synthesis of monofluorinated analogs of 2-tertiary hydroxyl-3-methyl-substituted carboxylic acidl derivatives |
| title_full | Asymmetric Michael addition of 5 H-oxazol-4-ones to vinyl sulfones : stereoselective synthesis of monofluorinated analogs of 2-tertiary hydroxyl-3-methyl-substituted carboxylic acidl derivatives |
| title_fullStr | Asymmetric Michael addition of 5 H-oxazol-4-ones to vinyl sulfones : stereoselective synthesis of monofluorinated analogs of 2-tertiary hydroxyl-3-methyl-substituted carboxylic acidl derivatives |
| title_full_unstemmed | Asymmetric Michael addition of 5 H-oxazol-4-ones to vinyl sulfones : stereoselective synthesis of monofluorinated analogs of 2-tertiary hydroxyl-3-methyl-substituted carboxylic acidl derivatives |
| title_short | Asymmetric Michael addition of 5 H-oxazol-4-ones to vinyl sulfones : stereoselective synthesis of monofluorinated analogs of 2-tertiary hydroxyl-3-methyl-substituted carboxylic acidl derivatives |
| title_sort | asymmetric michael addition of 5 h oxazol 4 ones to vinyl sulfones stereoselective synthesis of monofluorinated analogs of 2 tertiary hydroxyl 3 methyl substituted carboxylic acidl derivatives |
| topic | DRNTU::Science::Chemistry::Physical chemistry::Catalysis |
| url | https://hdl.handle.net/10356/106585 http://hdl.handle.net/10220/25011 http://dx.doi.org/10.1002/adsc.201400649 |
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