title: Chiral Primary Amine Catalyzed Asymmetric α-Benzylation with In Situ Generated ortho-Quinone Methides.
abstract: A dual activation strategy integrating primary amine catalysis and Lewis base activation has been developed for an asymmetric α-benzylation reaction. Enamines derived from β-ketocarbonyls could react effectively with in situ generated ortho-quinone methides under Lewis base activation in asymmetric α-benzylation of β-ketocarbonyls and α-branched aldehydes. The approach enables the creation of acyclic all-carbon quaternary stereocenters with excellent enantioselectivities and good activity.
authors.affiliation: Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
authors.forename: Yunbo
authors.initials: Y
authors.lastname: Zhu
authors.affiliation: Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
authors.forename: Wen-Zhao
authors.initials: WZ
authors.lastname: Zhang
authors.affiliation: Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
authors.forename: Long
authors.initials: L
authors.lastname: Zhang
authors.affiliation: Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
authors.forename: Sanzhong
authors.initials: S
authors.lastname: Luo
keywords: Lewis bases; asymmetric synthesis; chiral primary amine; o-quinone methide; β-ketocarbonyls