Thermodynamic control of diastereoselectivity in the formal nucleophilic substitution of bromocyclopropanes.
A new, general, and chemoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides is described. A wide range of alcohols and phenols can be employed as pronucleophiles in this transformation, providing expeditious access to trans-cyclopropanol ethers. A new mode of the selectivity control through a thermodynamic equilibrium is realized, alternative to the previously described steric and directing modes.
Banning
Joseph E
JE
Department of Chemistry, University of Kansas, 1251 Wesoce Hall Drive, Lawrence, Kansas 66045-75832, USA.
Prosser
Anthony R
AR
Rubin
Michael
M
D003521:Cyclopropanes / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013816:Thermodynamics
D003521:Cyclopropanes; D004987:Ethers; D004988:Ethers, Cyclic; C043657:cyclopropanol