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C2-symmetric functionalized azolium salt from serine ester for Cu-catalyzed asymmetric conjugate addition reaction.
- Source :
-
Journal of Molecular Catalysis A: Chemistry . Dec2014, Vol. 395, p66-71. 6p. - Publication Year :
- 2014
-
Abstract
- C 2 -symmetric ester-amide functionalized azolium salt was synthesized from readily available α-amino ester such as L -serine methyl ester. The combination of a Cu salt and the chiral azolium salt promoted the asymmetric conjugate addition reaction of enones with dialkylzincs. Thus, treatment of acyclic enone such as chalcone with Et 2 Zn afforded the corresponding 1,4-adduct with up to 85% ee. An excellent ee value of 93% was obtained when 3-nonen-2-one was reacted with Et 2 Zn. The present catalytic system was found to be useful for the 1,4-addition reaction of cyclic enone. For example, the reaction of 2-cyclohepten-1-one with Et 2 Zn produced ( R )-3-ethylcycloheptanone with 80% ee. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 13811169
- Volume :
- 395
- Database :
- Academic Search Index
- Journal :
- Journal of Molecular Catalysis A: Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 99736190
- Full Text :
- https://doi.org/10.1016/j.molcata.2014.08.006