Stereocontrolled Synthesis of Polysubstituted Housanes via gem-Bismetalated Cyclopropanes
Noam Orbach1, Rahul Suresh1, Ilan Marek1
1Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis, Technion-Israel Institute of Technology, Haifa 3200009, Israel.
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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