A new approach to switching of enantioselectivity in NHC-Cu-catalyzed conjugate addition of alkylzincs to cyclic enones.
Conjugate addition of Et(2)Zn to 2-cyclohexen-1-one catalyzed by Cu(OTf)(2) combined with an azolium salt derived from (S)-leucinol produced the corresponding (S)-adduct, while the use of Cu(acac)(2) in combination with the same ligand afforded the (R)-adduct as a major product.
Okamoto
Masaki
M
Department of Chemistry and Materials Engineering & High Technology Research Centre, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka, 564-8680, Japan.
Yamamoto
Yuko
Y
Sakaguchi
Satoshi
S
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003512:Cyclohexanones / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000480:Alkynes; D003512:Cyclohexanones; D006571:Heterocyclic Compounds; D008698:Mesylates; C030011:carbene; C028215:2-cyclohexen-1-one; D003300:Copper; D015032:Zinc; C012077:trifluoromethanesulfonic acid; D008697:Methane