Copper-catalyzed enantioselective conjugate addition of Grignard reagents to acyclic enones using monodentate phosphoramidite ligands

Tetrahedron Letters

Volumn 49, Issue 11, 2008, Pages 1877-1880

  Maciá, Beatriz ^a   Fernández Ibáñez, M Ángeles ^a   Mršić, Nataša ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Asymmetric catalysis; Conjugate addition; Grignard reagents; Phosphoramidites

Indexed keywords

COPPER; KETONE DERIVATIVE; LIGAND; ORGANOMETALLIC COMPOUND; PHOSPHORAMIDOUS ACID DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CONJUGATION; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; GRIGNARD REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 38949200990     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.019     Document Type: Article

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30. 2 (5 mol %), toluene (2 mL), -30 °C, 1 h.
31. For the preparation of ligands L3 and L4, see Supplementary data.
32. 2 (5 mol %) at -30 °C in dichloromethane and diethyl ether resulted in 10-20% ee.
33. Grignard reagent solutions in diethyl ether caused a drastic drop in enantioselectivity.
34. Addition of the substrate to the mixture of Grignard reagent and phosphoramidite complex led to a decrease in enantioselectivity.