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Synthesis 2018; 50(22): 4483-4489
DOI: 10.1055/s-0037-1610184
DOI: 10.1055/s-0037-1610184
paper
Derivatives of Alkyl 2-Hydroxy-3-oxocyclopent-1-enecarboxylates and Intermolecular [4+2] Cycloadditions of Cyclopentadienones Prepared Therefrom
This work was supported by the National Science Foundation (CHE-0910208) to whom we are grateful.Further Information
Publication History
Received: 04 May 2018
Accepted: 18 May 2018
Publication Date:
05 July 2018 (online)
![](https://www.thieme-connect.de/media/synthesis/201822/lookinside/thumbnails/ss-2018-c0307-op_10-1055_s-0037-1610184-1.jpg)
Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday.
Abstract
Some derivatives of alkyl 2-hydroxy-3-oxocyclopent-1-enecarboxylates have been synthesized and their reactivity as progenitors of cyclopentadienones for intermolecular [4+2]-cycloaddition reactions has been evaluated. It was found that the derivative containing a phosphate ester leaving group gave better yields in the cycloaddition reaction among the derivatives studied. The yields of the cycloaddition reactions were moderate, perhaps due side reactions not leading to the reactive intermediate cyclopentadienone.
Key words
cycloaddition - cyclopentadienones - Diels–Alder reaction - carbocycles - phosphorylation - reactive intermediatesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610184.
- Supporting Information
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References
- 1 Current address: Aswin Garimalla, Adesis - A Universal Display Company, New Castle, Delaware 19720.
- 2a Karunakaran J. Mohanakrishnan AK. Org. Lett. 2018; 20: 966
- 2b Prati L. Mancinelli M. Ciogli A. Mazzanti A. Org. Biomol. Chem. 2017; 15: 8720
- 2c Del Grosso A. Chamberlain AE. Clarkson GJ. Wills M. Dalton Trans. 2018; 47: 1451
- 2d Dong S. Qin T. Hamel E. Beutler JA. Porco JA. J. Am. Chem. Soc. 2012; 134: 19782
- 2e Isobe H. Sato S. Tanaka T. Tokuyama H. Nakamura E. Org. Lett. 2004; 6: 3569
- 2f Pearson AJ. Kim JB. Org. Lett. 2003; 5: 2457
- 2g Ogliaruso MA. Romanelli MG. Becker EI. Chem. Rev. 1965; 65: 261
- 3a DePuy CH. Isaks M. Eilers KL. Chem. Ind. 1961; 429
- 3b DePuy CH. Isaks M. Eilers KL. Morris GF. J. Org. Chem. 1964; 29: 3503
- 4 Harmata M. Barnes CL. Brackley J. Bohnert G. Kurti L. Rashatasakhon P. J. Org. Chem. 2001; 66: 5232
- 5a Pearson AJ. Kim JB. Tetrahedron Lett. 2003; 44: 8525
- 5b Basra SK. Drew MG. B. Mann J. Kane PD. J. Chem. Soc., Perkin Trans. 1 2000; 3592
- 5c Dols PP. M. A. Klunder JH. Zwanenburg B. Tetrahedron 1994; 50: 8515
- 5d Dols PP. M. A. Lacroix L. Klunder AJ. H. Zwanenburg B. Tetrahedron Lett. 1991; 32: 3739
- 6 Nantz MH. Fuchs PL. J. Org. Chem. 1987; 52: 5298
- 7 Harmata M. Gomes MG. Eur. J. Org. Chem. 2006; 2273
- 8 Jõgi A. Ilves M. Paju A. Pehk T. Kailas T. Muurisepp A. Lopp M. Tetrahedron: Asymmetry 2008; 19: 628
-
9
Krapcho PA.
Weimaster JF.
Eldridge JM.
Jahngen EG. E. Jr.
Lovey AJ.
Stephens WP.
J. Org. Chem. 1978; 43: 138
- 10 Thomas JB. Waas JR. Harmata M. Singleton DA. J. Am. Chem. Soc. 2008; 130: 14544
- 11 Inoue K. Sakai K. Tetrahedron Lett. 1976; 17: 4107
- 12 Staudinger H. Ruzicka L. Helv. Chim. Acta 1924; 7: 377