Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans
A Brønsted acid-catalyzed method to prepare tri- and tetrasubstituted furans efficiently from cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds is described. By taking advantage of the orthogonal modes of reactivity of the alcoholic substrate through slight modificat...
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| Format: | Journal Article |
| Language: | English |
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2013
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| Online Access: | https://hdl.handle.net/10356/96148 http://hdl.handle.net/10220/17133 |
| _version_ | 1811695986792202240 |
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| author | Mothe, Srinivasa Reddy Lauw, Sherman Jun Liang Kothandaraman, Prasath Chan, Philip Wai Hong |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Mothe, Srinivasa Reddy Lauw, Sherman Jun Liang Kothandaraman, Prasath Chan, Philip Wai Hong |
| author_sort | Mothe, Srinivasa Reddy |
| collection | NTU |
| description | A Brønsted acid-catalyzed method to prepare tri- and tetrasubstituted furans efficiently from cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds is described. By taking advantage of the orthogonal modes of reactivity of the alcoholic substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. At room temperature, p-TsOH·H2O-mediated tandem alkylation/cycloisomerization of the propargylic 1,4-diol with the β-dicarbonyl compound was found to selectively occur to provide the tetrasubstituted furan product. On the other hand, increasing the reaction temperature to 80 °C was discovered to result in preferential p-TsOH·H2O-catalyzed dehydrative rearrangement of the unsaturated alcohol and formation of the 2,3,5-trisubstituted furan adduct. |
| first_indexed | 2024-10-01T07:32:11Z |
| format | Journal Article |
| id | ntu-10356/96148 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:32:11Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | ntu-10356/961482020-03-07T12:37:08Z Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans Mothe, Srinivasa Reddy Lauw, Sherman Jun Liang Kothandaraman, Prasath Chan, Philip Wai Hong School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry A Brønsted acid-catalyzed method to prepare tri- and tetrasubstituted furans efficiently from cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds is described. By taking advantage of the orthogonal modes of reactivity of the alcoholic substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. At room temperature, p-TsOH·H2O-mediated tandem alkylation/cycloisomerization of the propargylic 1,4-diol with the β-dicarbonyl compound was found to selectively occur to provide the tetrasubstituted furan product. On the other hand, increasing the reaction temperature to 80 °C was discovered to result in preferential p-TsOH·H2O-catalyzed dehydrative rearrangement of the unsaturated alcohol and formation of the 2,3,5-trisubstituted furan adduct. 2013-10-31T06:52:27Z 2019-12-06T19:26:20Z 2013-10-31T06:52:27Z 2019-12-06T19:26:20Z 2012 2012 Journal Article Mothe, S. R., Lauw, S. J. L., Kothandaraman, P., & Chan, P. W. H. (2012). Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans. The journal of organic chemistry, 77(16), 6937-6947. https://hdl.handle.net/10356/96148 http://hdl.handle.net/10220/17133 10.1021/jo301093f en The journal of organic chemistry |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Mothe, Srinivasa Reddy Lauw, Sherman Jun Liang Kothandaraman, Prasath Chan, Philip Wai Hong Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans |
| title | Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans |
| title_full | Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans |
| title_fullStr | Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans |
| title_full_unstemmed | Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans |
| title_short | Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans |
| title_sort | bronsted acid catalyzed cycloisomerization of but 2 yne 1 4 diols with or without 1 3 dicarbonyl compounds to tri and tetrasubstituted furans |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/96148 http://hdl.handle.net/10220/17133 |
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