A Brønsted base-promoted diastereoselective dimerization of azlactones

A novel Brønsted base system for the diastereoselective dimerization of azlactones using trichloroacetate salts and acetonitrile has been developed. Desired products were obtained in good yields (60–93%) and with up to >19:1 dr after one hour of reaction. Additionally, the relative stereochemistr...

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Main Authors:	Danielle L. J. Pinheiro, Gabriel M. F. Batista, Pedro P. de Castro, Leonã S. Flores, Gustavo F. S. Andrade, Giovanni W. Amarante
Format:	Article
Language:	English
Published:	Beilstein-Institut 2017-12-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	azlactones dimerization diasteoreselective synthesis kinetics streptopyrrolidine analogue
Online Access:	https://doi.org/10.3762/bjoc.13.264

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spelling	doaj-07f9ccbbd7704b2bb38b8ecf999623a62021-02-02T00:48:48ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-12-011312663267010.3762/bjoc.13.2641860-5397-13-264A Brønsted base-promoted diastereoselective dimerization of azlactonesDanielle L. J. Pinheiro0Gabriel M. F. Batista1Pedro P. de Castro2Leonã S. Flores3Gustavo F. S. Andrade4Giovanni W. Amarante5Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária, São Pedro, Juiz de Fora, MG, CEP 36036-900, BrazilChemistry Department, Federal University of Juiz de Fora, Cidade Universitária, São Pedro, Juiz de Fora, MG, CEP 36036-900, BrazilChemistry Department, Federal University of Juiz de Fora, Cidade Universitária, São Pedro, Juiz de Fora, MG, CEP 36036-900, BrazilChemistry Department, Federal University of Juiz de Fora, Cidade Universitária, São Pedro, Juiz de Fora, MG, CEP 36036-900, BrazilChemistry Department, Federal University of Juiz de Fora, Cidade Universitária, São Pedro, Juiz de Fora, MG, CEP 36036-900, BrazilChemistry Department, Federal University of Juiz de Fora, Cidade Universitária, São Pedro, Juiz de Fora, MG, CEP 36036-900, BrazilA novel Brønsted base system for the diastereoselective dimerization of azlactones using trichloroacetate salts and acetonitrile has been developed. Desired products were obtained in good yields (60–93%) and with up to >19:1 dr after one hour of reaction. Additionally, the relative stereochemistry of the major dimer was assigned as being trans, by X-ray crystallographic analysis. The kinetic reaction profile was determined by using 1H NMR reaction monitoring and revealed a second order overall kinetic profile. Furthermore, by employing this methodology, a diastereoselective total synthesis of a functionalized analogue of streptopyrrolidine was accomplished in 65% overall yield.https://doi.org/10.3762/bjoc.13.264azlactonesdimerizationdiasteoreselective synthesiskineticsstreptopyrrolidine analogue
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Danielle L. J. Pinheiro Gabriel M. F. Batista Pedro P. de Castro Leonã S. Flores Gustavo F. S. Andrade Giovanni W. Amarante
spellingShingle	Danielle L. J. Pinheiro Gabriel M. F. Batista Pedro P. de Castro Leonã S. Flores Gustavo F. S. Andrade Giovanni W. Amarante A Brønsted base-promoted diastereoselective dimerization of azlactones Beilstein Journal of Organic Chemistry azlactones dimerization diasteoreselective synthesis kinetics streptopyrrolidine analogue
author_facet	Danielle L. J. Pinheiro Gabriel M. F. Batista Pedro P. de Castro Leonã S. Flores Gustavo F. S. Andrade Giovanni W. Amarante
author_sort	Danielle L. J. Pinheiro
title	A Brønsted base-promoted diastereoselective dimerization of azlactones
title_short	A Brønsted base-promoted diastereoselective dimerization of azlactones
title_full	A Brønsted base-promoted diastereoselective dimerization of azlactones
title_fullStr	A Brønsted base-promoted diastereoselective dimerization of azlactones
title_full_unstemmed	A Brønsted base-promoted diastereoselective dimerization of azlactones
title_sort	brønsted base-promoted diastereoselective dimerization of azlactones
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2017-12-01
description	A novel Brønsted base system for the diastereoselective dimerization of azlactones using trichloroacetate salts and acetonitrile has been developed. Desired products were obtained in good yields (60–93%) and with up to >19:1 dr after one hour of reaction. Additionally, the relative stereochemistry of the major dimer was assigned as being trans, by X-ray crystallographic analysis. The kinetic reaction profile was determined by using 1H NMR reaction monitoring and revealed a second order overall kinetic profile. Furthermore, by employing this methodology, a diastereoselective total synthesis of a functionalized analogue of streptopyrrolidine was accomplished in 65% overall yield.
topic	azlactones dimerization diasteoreselective synthesis kinetics streptopyrrolidine analogue
url	https://doi.org/10.3762/bjoc.13.264
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A Brønsted base-promoted diastereoselective dimerization of azlactones

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