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

SCOPUSTM   
Citations 20

38
checked on Aug 31, 2020

WEB OF SCIENCETM
Citations 50

36
checked on Oct 26, 2020

Page view(s) 50

241
checked on Oct 28, 2020

Google ScholarTM

Check

Altmetric


Plumx

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