In light of widespread advances in asymmetric methods, aldol reactions of carbonyl functionalities led to significant developments in the area of asymmetric synthesis. Recently, we have disclosed a new aldol method of the allenoate process in forming 2-hydroxy allenolate in high levels of enantioselectivity. For this method the reactin exclusively dictates a regioselectivity starting from methyl allenoate. As part of our continuous investigations utilizing allenoates as versatile substrates for asymmetric carbonyl additions, we establish stereospecific formation of gamma-addition adduct from 2-alkyl allenoates to construct axial and center chiralities during the reaction, which allows in good yields and excellent stereoselectivities. Reaction usually produced only single regio- and stereisomer. We would like to present herein scope and limitation of the reaction and its synthetic applications to bioactive natural product (+)-phellilane D.