The catalytic enantioselective diboration of terminal alkenes, combined with Pd-catalysed cross-coupling, provides aflexible platform for the construction of a broad array of chiral compounds from non-functionalized terminal alkenes. Although application of this methodology in target-oriented synthesis is easy to foresee, when one considers the tremendous variety of a-olefins and aryl/vinyl electrophiles that are available, the DCC reaction sequence should also provide new strategies for diversity-based synthesis. In addition to its direct impact on molecular synthesis, the studies presented here define a unique reactivity characteristic of 1,2-bis(pinacol boronates). We anticipate that the enhanced reactivity of the 1,2-bis(boronate) in transmetallation reactions may enable a range of other important enantioselective terminal alkene transformations that will have an impact on the field of chemical synthesis.

Scott N. Mlynarski, Christopher H. Schuster& James P. Morken Nature 2014, 505, 386–390.

Link: http://www.nature.com/nature/journal/v505/n7483/pdf/nature12781.pdf