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With the guiding principle from electronic helix theory we developed, reported here was the critical yet long-overlooked role of electronic polarizability effect in controlling absolute stereochemical courses of general asymmetric induction events.Thus, a sensitive dependence of the sense of chiral induction on an alkene substrates substituent electronic polarizability was uncovered from a range of structurally highly comparable Sharpless asymmetric dihydroxylation (AD) systems, from which a new polarizability-based stereochemical model of predictive power was advanced.[1] The helix theory further explains why kinetic resolutions by AD is challenging and shows how it might be solved (with selectivity factors up to 400 and ee to ＞ 99.9％).