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Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal SN2′ Substitution of Bromocylopropanes

Straub, Hillary
; 
Ryabchuk, Pavel
; 
Rubina, Marina
; 
Rubin, Michael
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Abstract
Enantiomerically enriched cyclopropyl ethers, amines, and cyclopropylazole derivatives possessing three stereogenic carbon atoms in a small cycle are obtained via the diastereoselective, formal nucleophilic substitution of chiral, non-racemic bromocyclopropanes. The key feature of this methodology is the utilization of the chiral center of the cyclopropene intermediate, which governs the configuration of the two adjacent stereocenters that are successively installed via 1,4-addition/epimerization sequence.
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2022-10-20
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MDPI
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Chemistry Scholarly Works
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Keywords
Cyclopropenes, Cyclopropanes, Nucleophilic addition, Metal-templated reactions
Citation
Straub, H.; Ryabchuk, P.; Rubina, M.; Rubin, M. Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal SN2′ Substitution of Bromocylopropanes. Molecules 2022, 27, 7069. https://doi.org/10.3390/molecules27207069
URI
https://hdl.handle.net/1808/33799
DOI
10.3390/molecules27207069
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