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April 23, 2026Organic Letters0 citationsOpen Access

Stereoselective Synthesis and Functionalization of Acetylenic Boronic Esters

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PSPatrick SchäferUKUli Kazmaier

Key Points

  • The research explores the stereoselective synthesis and functionalization of acetylenic boronic esters for creating complex organic structures.
  • Conducted hydrozirconation of homopropargyl boronic esters to achieve selective functionalization.
  • Utilized metal-halogen exchange to produce reactive vinyl iodides for further reactions.
  • Employed Negishi couplings and Heck reactions to synthesize polyketide-like structures.
  • Successfully generated functionalized alkenes through selective transformations.
  • Demonstrated the preservation of boronic ester functionality during the synthesis process.
  • Produced polyketide-like structures relevant for natural product synthesis.

Abstract

Hydrozirconation of homopropargyl boronic esters, readily available by Matteson homologation, allows their selective functionalization while preserving the boronic ester functionality. Metal-halogen exchange yields reactive vinyl iodides, which can be further converted into functionalized alkenes via Negishi couplings and Heck reactions. These reactions are used to generate polyketide-like structures, which are relevant for the synthesis of natural products.

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Cite This Study

Schäfer et al. (2026) studied this question.

synapsesocial.com/papers/69e9b6aa85696592c86eb054https://doi.org/10.1021/acs.orglett.6c01093
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