Dual control of the selectivity in the formal nucleophilic substitution of bromocyclopropanes en route to densely functionalized, chirally rich cyclopropyl derivatives
Abstract
Densely substituted cyclopropanol and cyclopropylazole derivatives with three stereogenic carbons in the small cycle are obtained via a highly diastereoselective formal nucleophilic substitution of bromocyclopropanes. The chiral center at C-2 in bromocyclopropane dictates the configuration of the other two stereocenters that are successively installed via a sterically controlled addition of a nucleophile, followed by a thermodynamically driven epimerization of the resulting enolate intermediate.
Department(s)
Chemistry and Biochemistry
Document Type
Article
DOI
https://doi.org/10.1021/ol4027792
Publication Date
12-6-2013
Recommended Citation
Ryabchuk, Pavel, Andrew Edwards, Nikolay Gerasimchuk, Marina Rubina, and Michael Rubin. "Dual control of the selectivity in the formal nucleophilic substitution of bromocyclopropanes en route to densely functionalized, chirally rich cyclopropyl derivatives." Organic letters 15, no. 23 (2013): 6010-6013.
Journal Title
Organic Letters
