Ruthenium-Porphyrin-Catalyzed Carbenoid Transfer Reactions_图文.doc

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Ruthenium-Porphyrin-Catalyzed Carbenoid Transfer Reactions_图文.doc

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Ruthenium-Porphyrin-Catalyzed Carbenoid Transfer Reactions_图文 ACCOUNT Ruthenium–Porphyrin-Catalyzed Carbenoid Transfer Reactions 2685 Scheme 1 Scheme 2 affording the corresponding cyclopropane-containing lac-tones in up to 85% ee (Scheme2).14a Previously, only10% ee was obtained in the asymmetric intramolecularcyclopropanation catalyzed by a metalloporphyrin cata-lyst.35 We observed the formation of chiral (carbene)ruthenium–porphyrin complexes 7a–c (Scheme3) from the reactionof complex 3 with diazo compounds EDA,8 diazo(diphe-nyl)methane,14a and allyl diazo(phenyl)acetate,14a respec-Figure 4 tively. Complexes 7b and 7c were isolated in pure formand structurally characterized by X-ray crystal analysis,and 7b was found to be an active catalyst for the asymmet-ric cyclopropanation of styrenes with EDA.14a This sup- Figure 5 Synlett 2010, No. 18, 2681–2700