Stereochemical Control in the Matteson Reaction

The Matteson homologation is a highly versatile method for the stereoselective insertion of carbenoids into boronic esters. Through iterative application of the process, complex chiral molecules can be synthesized. The stereoselectivity of the reaction is determined by a chiral diol incorporated in the boronic ester. Upon iterative application, this results in an efficient use of chiral pool starting materials. With that, however, comes limited stereochemical variability. This review delves into boronate homologations that can address these particular limitations and highlights unsolved problems in the field.