Journal
SYNTHESIS-STUTTGART
Volume 52, Issue 23, Pages 3667-3674Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1706421
Keywords
desymmetrization; asymmetric synthesis; alkenyl lithium; quaternary carbon stereocenter; bicyclo[4.3.0]nonene
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Funding
- Japan Society for the Promotion of Science (JSPS)
- KAKENHI [JP17K08208]
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The enantioselective synthesis of a bicyclo[4.3.0]nonene derivative bearing a quaternary carbon stereocenter is achieved by employing a desymmetrization strategy involving an intramolecular addition. The intramolecular nucleophilic addition of a highly reactive carbanion generated from an alkenyl iodide in the presence of a chiral ligand occurs with discrimination of two keto carbonyl groups to give the corresponding bicyclic compound in 81% yield and 39% ee. Asymmetric synthesis via an intramolecular desymmetrization strategy using a chiral ligand-carbanion complex represents a complementary approach to using chiral organocatalysts or chiral ligand-transition-metal complexes.
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