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June 14, 2026Nature CommunicationsOpen Access

Direct Asymmetric α-C Conjugate Addition of Aminomethylphosphonate Enabled by Carbonyl/Iminium Double Organoactivation

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Authors

PJPengwei JiXYX Y YangWLWeibo Ling

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Overview

Randomized trial demonstrates enantioselective α-C conjugate addition in bioactive compounds, suggesting enhanced synthesis methods.

Key Points

  • This work aims to enhance the direct enantioselective α-C conjugate addition of aminomethylphosphonate to α,β-unsaturated ketones.
  • Utilized an organo-organo double activation strategy employing pyridoxal and pyrrolidine.
  • Enabled the transformation of aminomethylphosphonates into reactive carbanions and α,β-unsaturated ketones into iminium species.
  • Synthesized a range of chiral phosphonic 1-pyrrolines with varying structural diversity.
  • Achieved 99% yield with greater than 20:1 diastereomeric ratio and 99% enantiomeric excess.
  • Successfully extended methodology to one-pot synthesis of diverse quaternary α-aminophosphonate derivatives.

Cite This Study

Ji et al. (2026) studied this question.

synapsesocial.com/papers/6a2e4753b1cc60ccdea8be0bhttps://doi.org/10.1038/s41467-026-74370-9
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