The use of tricarbonyliron chemistry in asymmetric synthesis is of increasing importance. With this comes the need for efficient and reliable techniques for the production of enantiopure starting materials. The methods currently available, although effective, are often long winded and wasteful. The development of a chiral hydride abstraction reagent analogous to the triphenylcarbenium species would be of great value in terms of improved yields and simplification of strategy. This thesis details the development of a system based around the dibenzosuberane frame-work. Two different chiral biases have been introduced to the structure leading to a potential double stereodifferentiation effect. Substitution of the 'backbone' of the structure has yielded enantiomeric excesses of up to 54%. The smaller, chiral aryl bias has given e.e.s in the region of 10%. Moreover the synthetic route to the backbone substituted examples has been greatly improved and is now suitable for use on a multigram scale.