A versatile synthetic approach to planar chiral molecules from (E)-5-cyclononen-1-one (1) has been developed; these molecules have multifunctionalities with (E)-cyclononene skeleton. The newly synthesized keto-ester 3 having central chirality shows labile planar chirality. In contrast, enol derivative 4 and enyne 5 show robust planar chirality.
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Tomooka et al. (2011) studied this question.