Unknown

Dataset Information

0

Synthesis of 3-substituted isoxazolidin-4-ols using hydroboration-oxidation reactions of 4,5-unsubstituted 2,3-dihydroisoxazoles.


ABSTRACT: Isoxazolidines represent a very important class of N/O-containing heterocycles used as the key intermediates in the synthesis of more complex cyclic and acyclic compounds, including various biologically active molecules. Here, we present a fast and highly stereoselective approach towards both C-3/4-cis and C-3/4-trans isomers of 3-substituted isoxazolidin-4-ols. The strategy relies on a highly regio- and trans-stereoselective hydroboration-oxidation reaction of the 4,5-unsubstituted 2,3-dihydroisoxazoles with basic hydrogen peroxide. The consecutive oxidation/reduction route, sequentially employing Dess-Martin periodinane and ?-selectride, is used for the inversion of the C-3/4-trans relative configuration of the isoxazolidine ring. The significance of the method lies in its variability and applicability to a concise synthesis of various 4-hydroxyisoxazolidines, starting from the readily available C-alkyl/aryl-nitrones. The resemblance to 3-hydroxypyrrolidines certainly makes the 4-hydroxyisoxazolidines important and valuable structural fragments in drug discovery.

SUBMITTER: Dikosova L 

PROVIDER: S-EPMC7308612 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

altmetric image

Publications

Synthesis of 3-substituted isoxazolidin-4-ols using hydroboration-oxidation reactions of 4,5-unsubstituted 2,3-dihydroisoxazoles.

Dikošová Lívia L   Laceková Júlia J   Záborský Ondrej O   Fischer Róbert R  

Beilstein journal of organic chemistry 20200616


Isoxazolidines represent a very important class of N/O-containing heterocycles used as the key intermediates in the synthesis of more complex cyclic and acyclic compounds, including various biologically active molecules. Here, we present a fast and highly stereoselective approach towards both C-3/4-<i>cis</i> and C-3/4-<i>trans</i> isomers of 3-substituted isoxazolidin-4-ols. The strategy relies on a highly regio- and <i>trans</i>-stereoselective hydroboration-oxidation reaction of the 4,5-unsub  ...[more]

Similar Datasets

| S-EPMC5095816 | biostudies-literature
| S-EPMC3134311 | biostudies-literature
| S-EPMC3159533 | biostudies-literature
| S-EPMC2788676 | biostudies-literature
| S-EPMC9420225 | biostudies-literature
| S-EPMC8537374 | biostudies-literature
| S-EPMC2818504 | biostudies-literature
| S-EPMC7557996 | biostudies-literature
| S-EPMC2662741 | biostudies-literature
| S-EPMC4348089 | biostudies-literature