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The development of an efficient, straightforward approach for access to a wide range of enantioenriched boron-containing 2,3-disubstituted indolines via highly chemo-, diastereo-, and enantioselective copper-catalyzed intramolecular boraylative cyclization of readily available 2-styrylimines is reported. This reaction proceeds under very mild conditions and displays a high degree of functional group compatibility. The practicability of this approach is demonstrated by a gram-scale reaction and further transformations of the chiral borylated indolines.

A ligand-controlled regiodivergent and enantioselective copper-catalyzed intermolecular hydroallylation of alkynes with allylic phosphates and hydrosilanes has been achieved for the first time. The chiral bidentate sulfonate-containing N-heterocyclic carbene ligated CuCl complex leads to enantioenriched SN2′-type products, whereas the use of the IMesCuCl catalyst affords SN2-type products. Thus a range of chiral branched and achiral linear 1,4-dienes could be facilely synthesized from readily available alkynes in a regiodivergent manner.