Catalytic asymmetric conjugate addition on macrocyclic and acyclic enones. Synthesis of R-(-)-muscone

Synlett

Volumn , Issue 11, 1999, Pages 1811-1813

  Alexakis, Alexandre ^a   Benhaïm, Cyril ^a   Fournioux, Xavier ^a   Van Den Heuvel, Alexandra ^a   Levêque, Jean Marc ^a   March, Sebastien ^a   Rosset, Stephane ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Asymmetry; Catalysis; Conjugate addition; Copper; Dialkyl zinc; Muscone

Indexed keywords

ALKENE DERIVATIVE; COPPER DERIVATIVE; KETONE DERIVATIVE; MUSCONE; ORGANOMETALLIC COMPOUND; PHOSPHITE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; REACTION ANALYSIS;

EID: 0032723513     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2931     Document Type: Article

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39. 2Zn (2M sol. in toluene, 0.29 mL, 0.58 mmol) was added followed by a solution of enone 6 (90 mg, 0.4 mmol) in toluene (1 mL). The reaction was followed by GC until completion (3 h). Acidic work-up and silica gel chromatography gave 50 mg of R-(-)-muscone, identical with an authentic sample kindly provided by Firmenich S.A.