Organo-main-group chemistry (Boron)

Crotyl boranes react stereospecifically

 

Crotyl boronates react with aldehydes to produce alcohols. The reaction is stereospecific so that the geometry of the crotyl boronate determines the stereochemistry of the alcohol product. E- and Z-crotyl boronates produce different alcohols, CLICK the links below to see how each of the boronates react:

 

E-crotyl boronate

Z-crotyl boronate

Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207–2293.