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Synlett
DOI: 10.1055/a-2711-1520
Letter

Facile Preparation of Chiral 1,2-Amino Alcohols Containing Unsymmetrical Nα-secondary Alkyl Substituents

Authors

  • Houguang Shi

    1   School of Medicine, Shanghai University, Shanghai, China (Ringgold ID: RIN34747)

  • Yanhong Song

    2   Department of Chemistry, Shanghai University, Shanghai, China (Ringgold ID: RIN34747)

  • Hegui Gong 

    3   Department of Chemistry, Shanghai University, Shanghai, China

Supported by: National Natural Science Foundation of China 22271182
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To address the lack of general synthetic methods for accessing chiral 1,2-amino alcohols bearing unsymmetrical N-α-secondary alkyl groups (CAUA), 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-iodo acetals with aryl bromides.



Publication History

Received: 27 July 2025

Accepted after revision: 26 September 2025

Accepted Manuscript online:
26 September 2025

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