Stereocontrolled Synthesis of Polysubstituted Housanes via <i>gem</i> -Bismetalated Cyclopropanes

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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Publication Details

Journal
Journal of the American Chemical Society
Published
2026-03-17
DOI
https://doi.org/10.1021/jacs.6c02374
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.00
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article

Stereocontrolled Synthesis of Polysubstituted Housanes via gem -Bismetalated Cyclopropanes

Noam Orbach, Rahul Suresh, Ilan Marek
Journal of the American Chemical Society
Cyclopropane Reaction Mechanisms
article

Stereocontrolled Synthesis of Polysubstituted Housanes via gem -Bismetalated Cyclopropanes

Noam Orbach, Rahul Suresh, Ilan Marek
article en

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.

Journal of the American Chemical Society
Technion – Israel Institute of Technology (IL)
Openalex Percentile: Top 18%
Cyclopropane Reaction Mechanisms
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