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Synthesis of Functionalized Dialkyl Cyclobutane-1,1-dicarboxylates and Alkyl 5,6-Dihydro-4H-pyran-3-carboxylates via Michael-Induced Ring Closure of delta-chloro-alpha,beta-Unsaturated Diesters and Ketoesters

(2008) SYNLETT. p.2697-2701
Author
Organization
Abstract
Michael-induced ring closure (MIRC) of dimethyl 2-(3-chloro-2,2-dimethylpropylidene)malonate, upon treatment with sodium tert-butylthiolate, sodium methoxide or sodium cyanide in methanol, provided a short and efficient synthesis of new 2-functionalized cyclobutane-1,1-dicarboxylic esters. Under similar conditions, methyl 2-acetyl-5-chloro-4,4-dimethylpent-2-enoate afforded 4-functionalized methyl 5,6-dihydro-4H-pyran-3-carboxylates as the MIRC products.
Keywords
dihydropyrans, carboxylic esters, Michael-induced ring closure, cyclobutanes, cyclizations

Citation

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MLA
Mangelinckx, Sven, Bruno Vermaut, Roland Verhé, et al. “Synthesis of Functionalized Dialkyl Cyclobutane-1,1-dicarboxylates and Alkyl 5,6-Dihydro-4H-pyran-3-carboxylates via Michael-Induced Ring Closure of delta-chloro-alpha,beta-Unsaturated Diesters and Ketoesters.” SYNLETT 17 (2008): 2697–2701. Print.
APA
Mangelinckx, S., Vermaut, B., Verhé, R., & De Kimpe, N. (2008). Synthesis of Functionalized Dialkyl Cyclobutane-1,1-dicarboxylates and Alkyl 5,6-Dihydro-4H-pyran-3-carboxylates via Michael-Induced Ring Closure of delta-chloro-alpha,beta-Unsaturated Diesters and Ketoesters. SYNLETT, (17), 2697–2701.
Chicago author-date
Mangelinckx, Sven, Bruno Vermaut, Roland Verhé, and Norbert De Kimpe. 2008. “Synthesis of Functionalized Dialkyl Cyclobutane-1,1-dicarboxylates and Alkyl 5,6-Dihydro-4H-pyran-3-carboxylates via Michael-Induced Ring Closure of delta-chloro-alpha,beta-Unsaturated Diesters and Ketoesters.” Synlett (17): 2697–2701.
Chicago author-date (all authors)
Mangelinckx, Sven, Bruno Vermaut, Roland Verhé, and Norbert De Kimpe. 2008. “Synthesis of Functionalized Dialkyl Cyclobutane-1,1-dicarboxylates and Alkyl 5,6-Dihydro-4H-pyran-3-carboxylates via Michael-Induced Ring Closure of delta-chloro-alpha,beta-Unsaturated Diesters and Ketoesters.” Synlett (17): 2697–2701.
Vancouver
1.
Mangelinckx S, Vermaut B, Verhé R, De Kimpe N. Synthesis of Functionalized Dialkyl Cyclobutane-1,1-dicarboxylates and Alkyl 5,6-Dihydro-4H-pyran-3-carboxylates via Michael-Induced Ring Closure of delta-chloro-alpha,beta-Unsaturated Diesters and Ketoesters. SYNLETT. New York: Georg Thieme Verlag Stuttgart; 2008;(17):2697–701.
IEEE
[1]
S. Mangelinckx, B. Vermaut, R. Verhé, and N. De Kimpe, “Synthesis of Functionalized Dialkyl Cyclobutane-1,1-dicarboxylates and Alkyl 5,6-Dihydro-4H-pyran-3-carboxylates via Michael-Induced Ring Closure of delta-chloro-alpha,beta-Unsaturated Diesters and Ketoesters,” SYNLETT, no. 17, pp. 2697–2701, 2008.
@article{505615,
  abstract     = {Michael-induced ring closure (MIRC) of dimethyl 2-(3-chloro-2,2-dimethylpropylidene)malonate, upon treatment with sodium tert-butylthiolate, sodium methoxide or sodium cyanide in methanol, provided a short and efficient synthesis of new 2-functionalized cyclobutane-1,1-dicarboxylic esters. Under similar conditions, methyl 2-acetyl-5-chloro-4,4-dimethylpent-2-enoate afforded 4-functionalized methyl 5,6-dihydro-4H-pyran-3-carboxylates as the MIRC products.},
  author       = {Mangelinckx, Sven and Vermaut, Bruno and Verhé, Roland and De Kimpe, Norbert},
  issn         = {0936-5214},
  journal      = {SYNLETT},
  keywords     = {dihydropyrans,carboxylic esters,Michael-induced ring closure,cyclobutanes,cyclizations},
  language     = {eng},
  number       = {17},
  pages        = {2697--2701},
  publisher    = {Georg Thieme Verlag Stuttgart},
  title        = {Synthesis of Functionalized Dialkyl Cyclobutane-1,1-dicarboxylates and Alkyl 5,6-Dihydro-4H-pyran-3-carboxylates via Michael-Induced Ring Closure of delta-chloro-alpha,beta-Unsaturated Diesters and Ketoesters},
  url          = {http://dx.doi.org/10.1055/s-0028-1083506},
  year         = {2008},
}

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