Templated Assembly of Chiral Medium-Sized Cyclic Ethers
via 8‑endo-trig Nucleophilic
Cyclization of Cyclopropenes

Rubin, Michael

Templated Assembly of Chiral Medium-Sized Cyclic Ethers via 8‑endo-trig Nucleophilic Cyclization of Cyclopropenes

Posted on 2016-12-02 - 17:20

An efficient approach toward enantioenriched eight-membered heterocycles via the intramolecular formal substitution of bromocyclopropanes with oxygen-based nucleophiles has been developed. The reaction proceeds via a reactive cyclopropene intermediate, which undergoes a rapid 8-endo-trig cyclization affording cis-fused [6.1.0] bicyclic products exclusively. The quaternary chiral center in the cyclopropene governs the configuration of the other two stereocenters in the final product.

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Ryabchuk, Pavel; Matheny, Jonathon P.; Rubina, Marina; Rubin, Michael (2016). Templated Assembly of Chiral Medium-Sized Cyclic Ethers via 8‑endo-trig Nucleophilic Cyclization of Cyclopropenes. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.6b03068

https://doi.org/10.1021/acs.orglett.6b03068

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