 as 
 part of our ongoing effort to expand the scope of cross - coupling 
 reactions of alkyl electrophiles , we have pursued a strategy wherein 
 the nucleophilic coupling partner includes a pendant olefin ; after 
 transmetalation by such a substrate , if -migratory insertion 
 proceeds faster than direct cross - coupling , an additional carbon  carbon 
 bond and stereocenter can be formed . with the aid of a nickel / diamine 
 catalyst ( both components are commercially available ) , we have established 
 the viability of this approach for the catalytic asymmetric synthesis 
 of 2,3-dihydrobenzofurans and indanes . 
 furthermore , we 
 have applied this new method to the construction of the dihydrobenzofuran 
 core of fasiglifam , as well as to a cross - coupling with a racemic 
 alkyl electrophile ; in the latter process , the chiral catalyst controls 
 two stereocenters , one that is newly generated in a -migratory 
 insertion and one that begins as a mixture of enantiomers . 
Supplementary Material