Facile Preparation of Chiral 1,2-Amino Alcohols Containing Unsymmetrical N-α-Secondary Alkyl Substituents

Houguang Shi; Yanhong Song; Hegui Gong

doi:10.1055/a-2711-1520

Synlett, Table of Contents

Synlett
DOI: 10.1055/a-2711-1520

Letter

Facile Preparation of Chiral 1,2-Amino Alcohols Containing Unsymmetrical N-α-Secondary Alkyl Substituents

Authors

Houguang Shi

¹School of Medicine, Shanghai University, Shanghai, China
Yanhong Song

²Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, Shanghai, China
Hegui Gong

²Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, Shanghai, China

Abstract

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Abstract

To address the lack of general synthetic methods for accessing chiral 1,2-amino alcohols bearing unsymmetrical N-α-secondary-alkyl groups (CAUAs), we developed an efficient protocol based on diastereoselective addition of alkyl Grignard and MeLi reagents to (S)-3,3-dimethyl-1,7a-dihydro-3H,5H-pyrrolo [1,2-c]oxazol-5-one (2). Careful methanolysis of the resulting adducts provided diverse CAUAs featuring a terminal ester functionality. Notably, intermediate 11 served as a key precursor for the synthesis of BiOx ligand 12, which exhibited exceptional performance in catalyzing the Ni-catalyzed enantioselective coupling of α-iodoacetals with aryl bromides.

Keywords

Amino alcohols - Diastereoselectivity - Ligands - Nucleophilic addition - Hydrolysis

Full Text

References

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