Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/96148
Title: Brønsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans
Authors: Mothe, Srinivasa Reddy
Lauw, Sherman Jun Liang
Kothandaraman, Prasath
Chan, Philip Wai Hong
Keywords: DRNTU::Science::Chemistry::Organic chemistry
Issue Date: 2012
Source: 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.
Series/Report no.: The journal of organic chemistry
Abstract: 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.
URI: https://hdl.handle.net/10356/96148
http://hdl.handle.net/10220/17133
DOI: 10.1021/jo301093f
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

Google ScholarTM

Check

Altmetric


Plumx

Items in DR-NTU are protected by copyright, with all rights reserved, unless otherwise indicated.