Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2012; 44(16): 2567-2574
DOI: 10.1055/s-0032-1316548
DOI: 10.1055/s-0032-1316548
paper
Easy Access to Acetal-Spiroacetal-Enol Ethers by Tandem Dearomatization of a Furan Ring and Acetalization
Further Information
Publication History
Received: 08 April 2012
Accepted after revision: 16 May 2012
Publication Date:
02 July 2012 (online)

Abstract
A range of structurally novel acetal-spiroacetal-enol ethers were readily synthesized from 3-[5-(methoxymethyl)-2-furyl]propionaldehydes by dearomatization to form carbocations that were trapped intramolecularly by the formyl group with subsequent acetalization.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Lipshutz BH. Chem. Rev. 1986; 86: 795
- 1b Roche SP, Porco JA. Jr. Angew. Chem., Int. Ed. Engl. 1996; 35: 729
- 1c Bur SK, Padwa A. Chem. Rev. 2004; 104: 2401
- 2a Chen C.-H, Rao PD, Liao C.-C. J. Am. Chem. Soc. 1998; 120: 13254
- 2b Xiong H, Hsung RP, Berry CR, Rameshkumar C. J. Am. Chem. Soc. 2001; 123: 7174
- 2c Domingo LR, Aurell MJ. J. Org. Chem. 2002; 67: 959
- 2d Toró A, Deslongchamps P. J. Org. Chem. 2003; 68: 6847
- 2e Liu L, Gao Y, Che C, Wu N, Wang DZ, Li C.-C, Yang Z. Chem. Commun. (Cambridge) 2009; 662
- 3a Gribble GW In Comprehensive Organic Synthesis . Vol. VIII. Trost BM, Fleming I. Pergamon; Oxford: 1991: 603
- 3b Donohoe TJ, Garg R, Stevenson CA. Tetrahedron: Asymmetry 1996; 7: 317
- 3c Donohoe TJ, Calabrese AA, Stevenson CA, Ladduwahetty T. J. Chem. Soc., Perkin Trans. 1 2000; 3724
- 4a Hodgson R, Majid T, Nelson A. J. Chem. Soc., Perkin Trans. 1 2002; 1631
- 4b Etchells LL, Sardarian A, Whitehead RC. Tetrahedron Lett. 2005; 46: 2803
- 4c McDermott PJ, Stockman RA. Org. Lett. 2005; 7: 27
- 4d Etchells LL, Helliwell M, Kershaw NM, Sardarian A, Whitehead RC. Tetrahedron 2006; 62: 10914
- 4e Georgiou T, Tofi M, Montagnon T, Vassilikogiannakis G. Org. Lett. 2006; 8: 1945
- 5a Zhou X, Wu W, Liu X, Lee C.-S. Org. Lett. 2008; 10: 5525
- 5b Abrams JN, Babu RS, Guo H, Le D, Le J, Osbourn JM, O’Doherty GA. J. Org. Chem. 2008; 73: 1935
- 5c Kallinen A, Tois J, Sjöholm R, Franzén R. Tetrahedron: Asymmetry 2010; 21: 2367
- 5d Hatano M, Mizuno T, Ishihara K. Chem. Commun. (Cambridge) 2010; 46: 5443
- 5e Noutsias D, Kouridaki A, Vassilikogiannakis G. Org. Lett. 2011; 13: 1166
- 5f Egan BA, Paradowski M, Thomas LH, Marquez R. Org. Lett. 2011; 13: 2086
- 6a Harris JM, Padwa A. J. Org. Chem. 2003; 68: 4371
- 6b Yim H.-K, Wong HN. C. J. Org. Chem. 2004; 69: 2892
- 6c Cong X, Liu K.-G, Liao Q.-J, Yao Z.-J. Tetrahedron Lett. 2005; 46: 8567
- 6d Bi J, Aggarwal KV. Chem. Commun. (Cambridge) 2008; 1: 120
- 6e Harris JM, Padwa A. Org. Lett. 2002; 4: 2029
- 7a Lee HK, Wong HN. C. Chem. Commun. (Cambridge) 2002; 18: 2114
- 7b Margaros I, Montagnon T, Vassilikogiannakis G. Org. Lett. 2007; 9: 5585
- 7c Margaros I, Vassilikogiannakis G. J. Org. Chem. 2008; 73: 2021
- 7d Pavlakos E, Georgiou T, Tofi M, Montagnon T, Vassilikogiannakis G. Org. Lett. 2009; 11: 4556
- 7e Dong J.-Q, Wong HN. C. Angew. Chem. Int. Ed. 2009; 48: 2351
- 8a Gao Y, Wu W.-L, Ye B, Zhou R, Wu Y.-L. Tetrahedron Lett. 1996; 37: 893
- 8b Gao Y, Wu W.-L, Wu Y.-L, Ye B, Zhou R. Tetrahedron 1998; 54: 12523
- 8c Yin B.-L, Yang Z.-M, Hu T.-S, Wu Y.-L. Synthesis 2003; 1995
- 8d Chen L, Xu H.-H, Yin B.-L, Xiao C, Hu T.-S, Wu Y.-L. J. Agric. Food Chem. 2004; 52: 6719
- 8e Yin B.-L, Hu T.-S, Wu Y.-L. Tetrahedron Lett. 2004; 45: 2017
- 8f Fan J.-F, Gao Y, Wu Y.-L. Synlett 2003; 309
- 8g Hu T.-S, Yue H.-J, Gao Y, Wu Y.-L. Synlett 2004; 306
- 8h Yin B.-L, Wu W.-M, Fan J.-F, Gao Y, Wu Y.-L. Eur. J. Org. Chem. 2003; 4016
- 9 Yin B.-L, Lai J.-Q, Zhang Z.-R, Jiang H.-F. Adv. Synth. Catal. 2011; 353: 1961
- 10 Casu L, Bonsignore L, Pinna M, Casu M, Floris C, Gertsch J, Cottiglia F. J. Nat. Prod. 2006; 69: 295
For reviews on the dearomatization of furan rings, see:
For selected recent examples of furan dearomatizations through Diels–Alder cycloadditions, see: