Synthesis of Vinyl Boronates from Aldehydes and Ketones by Peterson Olefination: Investigation of the Peterson/Boron‐Wittig Chemoselectivity

Abstract We report our results on the development of the Peterson olefination using gem ‐borylsilylmethane derivatives to synthesize di‐ and tri‐substituted vinyl boronates. We show that the electronic properties of the carbonyl partner have no effect on the Peterson/boron‐Wittig chemoselectivity whereas the nature of the silane group plays an important role. A DFT study helps explain observed reactivity, chemoselectivity and stereoseletivity