In this article, we describe asymmetric syntheses taking advantage of chiral auxiliary characteristics. In the asymmetric Michael addition reaction of chiral thiol, we developed a novel tandem Michael-MPV (Meerwein-Ponndorf-Verley) reaction, which provided the 1,3-mercaptoalcohols with two or three chiral centers. Moreover, multi-contiguous chiral centers were finely constructed in one pot utilizing three types of Michael addition-initiated reactions, i.e., tandem Michael-aldol reaction, double Michael addition reaction, double Michael-aldol reaction, which were triggered by a nucleophilic attack of a novel recyclable chiral amine. Asymmetric syntheses of a number of biologically active compounds such as captopril, γ-lactone natural products, (+)-negamycin and β-lactam were achieved as an application of our reactions.