PLANAR CHIRAL CP-ASTERISK-RU COMPLEXES .2. BIS(ALLYL) AND BIS(ARENE) COMPLEXES DERIVED FROM (R)-CARVONE

Reaction of [CpRuOMe](2) (1) with either enantiomer of the naturally occurring ketonic diterpene carvone or the trimethylsilyl enolate deri ved thereof leads to homochiral CpRu-pi-complexes 6-9, where the Cp*R u moiety is bound to either the exocyclic double bond or an allyl func tion derived from it as well as to an enone or ene system in the ring. Full aromatization of the cyclic enone under the same reaction condit ions was achieved with 7,8-dihydrocarbone or its trimethylsilyl enolat e, respectively, giving complexes 13 and 14. The carvacrole complex 14 (and consequently also 13) is shown by the NMR spectra of the diaster oisomers obtained through derivatization with (S)-camphorsulfonic acid to be homochiral, thus, central chirality of the carvone has been ful ly transformed into planar chirality of the carvacrole complex. Compou nds 6, 7 . BFB4 7 . CF3SO3, and 8 . CF3SO3, and 14 . CF3SO3 where char acterized by single-crystal X-ray analysis, which allowed for the dete rmination of the absolute configuration of the latter.