1997 Volume 55 Issue 10 Pages 886-896
The chemistry of compounds that contain a carbon atom substituted with three or four different reactive functional groups has received relatively little attention, despite the considerable theoretical and practical significance these compounds should have for synthetic organic chemistry. Among such compounds containing this multistructural motif, multifunctional carbons, those containing both the carbonyl group and halogens, along with other heteroatom functionalities, would seem to have particular value in synthetic chemistry. However, because of the inherent chemical instability of these structures as well as a paucity of synthetic approaches, the potential of this class of compound has not been realized. On the basis of these considerations, we have focused attention on the synthesis of a new class of compounds (the structure in Figure 1) incorporating into their structures a carbon atom on which an ester carbonyl, halogen (Br or F), and other non-carbon atom (N, 0, and/or S) are substituted. Advantages of using fluorine as the halogen include the stability of the C-F bond, as well as the fundamental chemical and biological interest in fluorine-containing compounds. The synthesis, reactions, spectral data, optical resolutions, and determinations of absolute configurations of examples of these multifunctional compounds are described.
