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Scope and limitations of optical pure hydantoins as chiral auxiliaries in asymmetric Mannich reactions

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Abstract

The Mannich reaction of various 5-substituted and N-acyl substituted chiral hydantoins with a series of aldimines smoothly occurred with full stereochemical control. These Mannich adducts have been cleaved by alcoholysis to afford several synthetically useful chiral building blocks like β-amino esters and β-lactams in good yields and in enantiopure form.

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Authors and Affiliations

  1. Hubei Collaborative Innovation Center for Advanced Organochemical Materials & Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan, 430062, P. R. China

    Feng Chen, Cuifen Lu, Junqi Nie, Zuxing Chen & Guichun Yang

Authors
  1. Feng Chen
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  2. Cuifen Lu
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  3. Junqi Nie
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  4. Zuxing Chen
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  5. Guichun Yang
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Corresponding author

Correspondence to Guichun Yang.

Additional information

Supported by the National Natural Science Foundation of China(No.21342002).

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Chen, F., Lu, C., Nie, J. et al. Scope and limitations of optical pure hydantoins as chiral auxiliaries in asymmetric Mannich reactions. Chem. Res. Chin. Univ. 32, 219–225 (2016). https://doi.org/10.1007/s40242-016-5273-9

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  • DOI: https://doi.org/10.1007/s40242-016-5273-9

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