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Chiral Primary Amine Catalyzed Asymmetric α‐Benzylation with In Situ Generated ortho ‐Quinone Methides
Author(s) -
Zhu Yunbo,
Zhang WenZhao,
Zhang Long,
Luo Sanzhong
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605302
Subject(s) - stereocenter , chemistry , amine gas treating , catalysis , lewis acids and bases , primary (astronomy) , organic chemistry , in situ , base (topology) , quinone , alkylation , combinatorial chemistry , organocatalysis , quaternary carbon , enantioselective synthesis , mathematical analysis , physics , mathematics , astronomy
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.