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Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans

หน่วยงาน Nanyang Technological University, Singapore

รายละเอียด

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.