The availability of efficient synthetic methods for achieving absolute stereoselectivity in the production of enantiomerically pure compounds is of considerable current interest in organic chemistry. Recently, we discovered a highly stereoselective synthesis of unusual gamma aldol adducts from the reaction of 2-alkyl allenoates with a chiral bromoborane in the presence of Hunig base, and then aldehydes. The characteristic features of our approaches in terms of structural aspects of the products have encouraged us to carry out more investigations. We have developed a method for the kinetic resolution of racemic aldehydes for this purpose. We present herein our discovery of control elements to regulate diastereoselective formation of a gamma adduct from the reaction of 2-alkyl allenoates with racemic aldehydes through a kinetic resolution, which allows in good yields with high levels of stereoselectivity as describe below. This simple laboratory process can also be operated in parallel and provides rapid access to gamma aldol adducts in pure form. We would like to present herein scope and limitation of the reaction and its synthetic applications to natural product, (+)-xylogiblactone.