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Morozova, Varvara; Skotnitzki, Juri; Moriya, Kohei; Karaghiosoff, Konstantin; Knochel, Paul (2018): Preparation of Optically Enriched Secondary Alkyllithium and Alkylcopper ReagentsSynthesis of (-)-Lardolure and Siphonarienal. In: Angewandte Chemie-International Edition, Vol. 57, No. 19: pp. 5516-5519
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Optically enriched secondary alkyl iodides were converted into secondary alkyllithium and secondary alkylcopper compounds with very high retention of configuration. Quenching with various electrophiles, including chiral epoxides, provided a range of chiral molecules with high enantiomeric purity (>90%ee). This method has been applied in an iterative fashion in the total synthesis of (-)-lardolure in 13 steps and 5.4% overall yield (>99%ee, dr>99:1) and siphonarienal in 15 steps and 5.6% overall yield (>99%ee, dr>99:1) starting from commercially available ethyl (R)-3-hydroxybutyrate (>99%ee).