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Asymmetric Michael Addition of β‐Ketoesters to Enones Catalyzed by the Lithium Salt of a Primary β‐Amino Acid
Author(s) -
Yoshida Masanori,
Kubara Ami,
Nagasawa Yuki,
Hara Shoji,
Yamanaka Masahiro
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201400024
Subject(s) - chemistry , michael reaction , enantioselective synthesis , salt (chemistry) , catalysis , adduct , lithium (medication) , decarboxylation , primary (astronomy) , addition reaction , organic chemistry , organocatalysis , amino acid , combinatorial chemistry , medicine , physics , astronomy , endocrinology , biochemistry
A highly enantioselective Michael addition of β‐ketoesters to enones was achieved by using the salt of a readily available primary β‐amino acid as the catalyst. The obtained Michael adducts were converted into enantioenriched 1,5‐diketones in high yields through a common decarboxylation reaction under acidic conditions. A plausible reaction mechanism for the Michael addition reaction, which is supported by results of mechanistic studies that include DFT calculations, is also described.