| ชื่อเรื่อง | : | Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans |
| นักวิจัย | : | Mothe, Srinivasa Reddy , Lauw, Sherman Jun Liang , Kothandaraman, Prasath , Chan, Philip Wai Hong |
| คำค้น | : | DRNTU::Science::Chemistry::Organic chemistry |
| หน่วยงาน | : | Nanyang Technological University, Singapore |
| ผู้ร่วมงาน | : | - |
| ปีพิมพ์ | : | 2555 |
| อ้างอิง | : | 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. , http://hdl.handle.net/10220/17133 , http://dx.doi.org/10.1021/jo301093f |
| ที่มา | : | - |
| ความเชี่ยวชาญ | : | - |
| ความสัมพันธ์ | : | The journal of organic chemistry |
| ขอบเขตของเนื้อหา | : | - |
| บทคัดย่อ/คำอธิบาย | : | 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. |
| บรรณานุกรม | : |
Mothe, Srinivasa Reddy , Lauw, Sherman Jun Liang , Kothandaraman, Prasath , Chan, Philip Wai Hong . (2555). Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans.
กรุงเทพมหานคร : Nanyang Technological University, Singapore. Mothe, Srinivasa Reddy , Lauw, Sherman Jun Liang , Kothandaraman, Prasath , Chan, Philip Wai Hong . 2555. "Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans".
กรุงเทพมหานคร : Nanyang Technological University, Singapore. 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."
กรุงเทพมหานคร : Nanyang Technological University, Singapore, 2555. Print. 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. กรุงเทพมหานคร : Nanyang Technological University, Singapore; 2555.
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