Many bioactive compounds contain cyclic moieties and stereogenic centers. While there are many preexisting cyclization reactions and ways to install stereocenters, new methods are constantly being developed. The Michael-initiated ring closure (MIRC) is a useful method to construct cyclic compounds in a diastereoselective fashion. We envisioned inducing enantioselectivity by utilizing chiral lithium amides as a noncovalent chiral auxiliary. We herein report a stereoselective MIRC reaction to construct 1,2-(trans)-disubstituted cycloalkanes between arylacetic acids and α,β-unsaturated esters. This method yields ring sizes varying from cyclopropane to cycloheptane with high diastereoselectivity (>20:1 dr) and enantioselectivity (up to 99% ee). We have also demonstrated the versatility of this method by showcasing the use of various aryl substituents and α-substitutents for the substrate acid as well as the use of different α,β-unsaturated esters and sulfone. In addition, we illustrated the utility of this method by applying it in the synthesis of a selective diacylglycerol acyltransferase (DGAT-1) inhibitor, A-922500, which could be further used to study its effects on obesity and insulin resistance.