84247-66-5Relevant academic research and scientific papers
Transition-metal Mediated Asymmetric Synthesis. Part 3. Preparation and Stereospecific Alkylation of Unsymmetrically Substituted Tricarbonyl(cyclohexadienyl)iron(1+) Salts: an Organometallic Approach to the Synthesis of Carvone, Cryptomerion, and Bilobanone
Stephenson, G. Richard
, p. 2449 - 2456 (2007/10/02)
Tricarbonyl(η5-3-methoxy-2-methylcyclohexa-2,4-dienyl)iron(1+)hexafluorophosphate(1-) has been prepared by a novel method based on thallium(III) oxidation.The opposite substitution pattern is obtained by hydride abstraction.Alkylation by bis(1-methylethenyl)cadmium, to introduce an olefinic side-chain, has been shown to be stereospecific for the α-face, and removal of the metal affords the expected enones. (+/-)-Carvone and -sylve-carvone have been prepared by this means.The results indicate the importance of regiocontrol of alkylation if chiral salts are to be employed in synthesis.
