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• W1968205611 endingPage "6907" @default.
• W1968205611 startingPage "6906" @default.
• W1968205611 abstract "A highly diastereoselective formal nucleophilic substitution of bromocyclopropanes with oxygen- and nitrogen-based nucleophiles was demonstrated. The reaction proceeds via a base-assisted dehydrohalogenation producing a cyclopropene intermediate, which subsequently undergoes addition of a pronucleophile across the strained double bond. Very high chemoselectivity toward addition of primary and secondary alkoxides, as well as N-nucleophiles, in the presence of tert-butoxide base was observed, whereas phenoxides did not undergo addition under these reaction conditions. Facial selectivity of the addition can be efficiently controlled either by sterics or through a directing effect of an amide, carboxylate, and an o-aminomethylphenol function. Employment of tethered optically active amino alcohols as pronucleophiles allowed for efficient assembly of homochiral bicyclic compounds." @default.
• W1968205611 created "2016-06-24" @default.
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• W1968205611 date "2009-05-04" @default.
• W1968205611 modified "2023-09-26" @default.
• W1968205611 title "Highly Diastereoselective Formal Nucleophilic Substitution of Bromocyclopropanes" @default.
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• W1968205611 doi "https://doi.org/10.1021/ja900634m" @default.
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