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A Bronsted base-promoted diastereoselective dimerization of azlactones.

ABSTRACT: 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.

SUBMITTER: Pinheiro DLJ 

PROVIDER: S-EPMC5753058 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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A Brønsted base-promoted diastereoselective dimerization of azlactones.

Pinheiro Danielle L J DLJ   Batista Gabriel M F GMF   de Castro Pedro P PP   Flores Leonã S LS   Andrade Gustavo F S GFS   Amarante Giovanni W GW  

Beilstein journal of organic chemistry 20171213

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 <i>trans</i>, by X-ray crystallographic analysis. The kinetic reaction profile was determined by using <sup>1</sup>H NMR reaction monitoring and revealed a seco  ...[more]