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An intersting extention of the concept of asymmetric selection via syn elimination2 lay in its application to medium-sized rings where the resulting cycloalkene may be produced in the chiral, trans form. The experiment would of necessity have to be carried out with an appropriately substituted cyclooctane, (1), for only the optically active trans-cyclooctenes (2a or 2b) possess a level of optical stability sufficient to survive the experimental conditions.
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