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This paper reports the synthesis and circular dichroism data of (1S)-2,4-adamantanedione-4-/sup 18/-O, a rigid 1,3-diketone, in which the chirality is solely due to the oxygen isotope. The synthetic route to this ketone is new, general, and applicable to a variety of chiral and achiral oxygen-18 labeled ketones. In addition to its novelty and generality this route appears to be more effective than the present methods of introduction of oxygen 18. The critical difference in the route we followed is the nonaqueous introduction of oxygen 18, through the intermediacy of an 1,2-(/sup 18/O)dioxetane.

Chirality due to oxygen-18 substitution. Synthesis and chiroptical properties of (1S)-2,4-adamantanedione-4-18O