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March 19, 2026Journal of the American Chemical Society4 citationsOpen Access

Stereocontrolled Synthesis of Polysubstituted Housanes via gem -Bismetalated Cyclopropanes

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NONoam OrbachRSRahul SureshIMIlan Marek

Key Points

  • This research aims to develop a method for synthesizing polysubstituted housanes with controlled stereochemistry.
  • Utilized bismetalated cyclopropane intermediates for synthesis.
  • Employed diastereoselective allylzincation of lithiated cyclopropenes.
  • Conducted intramolecular cyclization to form metalated housanes.
  • Performed electrophile trapping for diversification of the products.
  • Successfully synthesized 2,3-dialkyl-substituted housanes.
  • Demonstrated selective synthesis of both diastereomers.
  • Achieved high stereoselectivity in the intermediates.

Abstract

We report a stereoselective synthesis of polysubstituted housanes via bismetalated cyclopropane intermediates. The strategy relies on diastereoselective allylzincation of lithiated cyclopropenes followed by intramolecular cyclization, generating metalated housanes as key intermediates. Subsequent electrophile trapping enables efficient diversification of the housanes. Notably, this approach provides access to 2,3-dialkyl-substituted housanes, allowing the selective synthesis of both the diastereomers.

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Cite This Study

Orbach et al. (2026) studied this question.

synapsesocial.com/papers/69bb92df496e729e6298086dhttps://doi.org/10.1021/jacs.6c02374
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