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Rhodium(I)-Catalyzed O-H Insertions on O-Protected α-Diazo-β-Hydroxyesters.

Ophélie Montiège1, Florian Rouzier1, Jérôme Lhoste1

  • 1Institut des Molécules et Matériaux du Mans, IMMM-UMR 6283 CNRS, Le Mans Université, Avenue Olivier Messiaen, 72085 Cedex 9 Le Mans, France.

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|February 13, 2024
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This study introduces the first O-H insertion reaction for O-protected α-diazo-β-aryl-β-hydroxyesters. Rhodium(I) catalysts enable access to diverse α,β-dioxygenated esters, overcoming previous synthetic challenges.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • X-H insertion reactions are vital for molecular diversity via diazocarbonyl compounds.
  • X-H insertion on α-diazo-β-aryl-β-hydroxyester scaffolds has been a significant synthetic challenge.

Purpose of the Study:

  • To report the first successful O-H insertion reaction on O-protected α-diazo-β-aryl-β-hydroxyesters.
  • To provide a straightforward synthetic route to α,β-dioxygenated esters.

Main Methods:

  • Utilized Rh(I) catalysts to promote O-H insertion reactions.
  • Employed O-protected α-diazo-β-aryl-β-hydroxyesters as substrates.
  • Investigated the modulation of alcohol and aryl substituents.

Main Results:

  • Achieved the first O-H insertions on the challenging α-diazo-β-aryl-β-hydroxyester scaffold.
  • Synthesized 32 diverse α,β-dioxygenated esters in moderate to good yields.
  • Observed high diastereoselectivity (up to 7.5:1) favoring the syn isomer.

Conclusions:

  • Rhodium(I) catalysts are key to directing O-H insertion over competing migration pathways.
  • This methodology offers broad scope for synthesizing functionalized esters.
  • The reaction provides efficient access to valuable α,β-dioxygenated ester building blocks.