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. 2024 Nov 11;63(46):e202409226.
doi: 10.1002/anie.202409226. Epub 2024 Sep 20.

From Cyclopropene to Housane Derivatives Via Intramolecular Cyclopropanation

Darío Coto  1   2   3 , David Suárez-García  1   2   3 , Sergio Mata  1 , Israel Fernández  3   4 , Luis A López  1   2   3 , Rubén Vicente  1   2   3
Affiliations

From Cyclopropene to Housane Derivatives Via Intramolecular Cyclopropanation

Darío Coto et al. Angew Chem Int Ed Engl. .

Abstract

The synthesis of housane derivatives from cyclopropenes is described. Under rhodium(II) catalysis, cyclopropenylvinyl carbinols can regioselectively generate a carbene intermediate which undergoes an intramolecular cyclopropanation to form a housane, a skeleton with similar ring strain as the cyclopropene precursor. The procedure shows a remarkable broad scope and efficiency. Moreover, the method served to prepare man-made housane-containing terpene derivatives, which are not accessible by Nature.

Keywords: cyclopropenes; housanes; strained compounds; terpenes.

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References

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