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Highly Enantioselective Kinetic Resolution of Michael Adducts through N‐Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes
Author(s) -
Chen XiangYu,
Li Sun,
Liu Qiang,
Kumar Mukesh,
Peuronen Anssi,
Rissanen Kari,
Enders Dieter
Publication year - 2018
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.201802420
Subject(s) - kinetic resolution , enantioselective synthesis , carbene , adduct , diastereomer , chemistry , selectivity , enantiomer , michael reaction , catalysis , resolution (logic) , organocatalysis , combinatorial chemistry , organic chemistry , stereochemistry , computer science , artificial intelligence
A highly efficient strategy for the kinetic resolution of Michael adducts was realized using a chiral N‐heterocyclic carbene catalyst. The kinetic resolution provides a new convenient route to single diastereomers of cyclohexenes and Michael adducts in good yields with high enantiomeric excesses (up to 99 % ee with a selectivity factor of up to 458). This “two flies with one swat” concept allows the synthesis of these two synthetically valuable compound classes at the same time by a single transformation.