“Boron Ylide” Enables Stereoselective Construction of <i>gem</i> ‐Diborylcyclopropanes
Tongchang Fang, Peng Zhang, Chao Liu
Abstract
The stereoselective cyclopropanation of olefins with "boron ylide" is disclosed for the first time, providing a modular strategy for the synthesis of stereospecific diboryl-functionalized cyclopropanes. The chiral gem-diborylcyclopropanes are synthesized with excellent enantioselectivity with the aid of a chiral auxiliary. Based on the powerful transformable ability of boryl group, those challenging multi-quaternary carbon centers in cyclopropane units have been facilely constructed with excellent stereoselectivity. Control experiments indicate that the boryl groups are necessary for both chemoselectivity and stereoselectivity control.
Topics & Concepts
StereoselectivityBoronYlideIsotopes of boronChemistryStereochemistryOrganic chemistryCatalysisOrganoboron and organosilicon chemistrySynthesis and characterization of novel inorganic/organometallic compoundsFerrocene Chemistry and Applications