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February 28, 20260 citationsOpen Access

Analysis of cyclohexa-1,4-dienes with an asymmetrically substituted, 3° carbon atom as chiral dihydrogen surrogates in reagent-controlled transfer hydrogenation of alkenes

PRPaul E. RuckerMOMartin Oestreich

Key Points

  • The aim is to investigate the use of chiral cyclohexa-1,4-diene-based dihydrogen surrogates in transfer hydrogenation.
  • Synthesis of chiral cyclohexa-1,4-diene-based dihydrogen surrogates.
  • Application of these surrogates in the reduction of 1,1-disubstituted alkenes.
  • Comparison of experimental results with computational predictions.
  • Investigation of structure-selectivity relationships influenced by steric factors.
  • Synthesis of a broad set of chiral surrogates expanded structural diversity.
  • Results align with computational predictions regarding efficiency.
  • Steric factors near and far from the stereocenter significantly influence transfer hydrogenation efficiency.

Abstract

Building on a reagent-controlled, trityl-cation-initiated enantioselective transfer hydrogenation of alkenes recently developed by us, a broad set of chiral cyclohexa-1,4-diene-based dihydrogen surrogates was synthesized and applied to the reduction of 1,1-disubstituted alkenes. The expanded structural diversity allowed for a more refined investigation of the structure-selectivity relationship. The experimental results are in agreement with earlier computational predictions and highlight the role of steric factors proximal (gray circle) and distal (black circle) to the stereocenter in governing the efficiency of transfer hydrogenation.

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Cite This Study

Rucker et al. (2025) studied this question.

synapsesocial.com/papers/69a286a70a974eb0d3c01b79https://doi.org/10.14279/depositonce-24650
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