In some cases, chelation of the substituents with the metal catalyst (e.g., lithium or magnesium) can have a significant influence on the stereochemistry of the reaction. Chelation can direct the approach of reagents and control the stereochemistry.
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cis-2-methyl 3-phenylthiocyanomethyl cyclohexanone
(S)-2,2-Dimethyl-3-((R)-2-morpholin-4-yl-2-oxo-1-phenyl-ethylamino)-3-phenyl-propionic acid ethyl ester
(1R*,2R*,3R*)-1,2-diphenyl-1,3-dimethoxybutane
benzyl 2,3,4-trideoxy-2-N-piperidino-3-(p-tolylsulfinyl)-α-D-erythro-hex-3-enopyranoside
