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Synthesis 2021; 53(04): 688-698
DOI: 10.1055/s-0040-1706543
DOI: 10.1055/s-0040-1706543
paper
Highly Diastereoselective Reactions of Isoxazolidine-4,5-diols with Grignard Reagents: A New Approach to anti,syn-γ-Amino-α,β-diols
This work was supported by the Slovak Grant Agency for Science VEGA (Project no. 1/0552/18), and the Research and Development Operational Programmes funded by the European Regional Development Fund (ERDF) (ITMS Project nos. 26240120001 and 26240120025). This article was also created with the support of the MŠVVaŠ of the Slovak Republic within the Research and Development Operational Programme for the project ‘University Science Park of STU Bratislava’ (ITMS Project no. 26240220084) co-funded by the European Regional Development Fund.
Abstract
An investigation of the reaction of 3,4-trans-isoxazolidine-4,5-diols with Grignard reagents is described for the first time. Their resemblance to five-membered cyclic hemiacetals allows them to react as α-hydroxy-β-(hydroxyamino)aldehydes in a highly stereoselective manner, providing anti,syn-γ-(hydroxyamino)-α,β-diols in moderate yields and with good to excellent syn-diastereoselectivities, which can be improved by the addition of anhydrous cerium chloride. The obtained (hydroxyamino)diols serve as suitable precursors of anti,syn-γ-amino-α,β-diols that represent valuable scaffolds for the synthesis of various biologically active compounds.
Key words
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isoxazolidines -
amino diols -
Grignard reaction -
diastereoselectivity -
crystal structure
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706543.
- Supporting Information
Publication History
Received: 16 August 2020
Accepted after revision: 23 September 2020
Article published online:
29 October 2020
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