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Preparation of a Chiral Building Block by an Organocatalytic Asymmetric Intramolecular Michael Reaction
Author(s) -
Sato Yusuke,
Hosoya Yosuke,
Kobayashi Ikumi,
Adachi Kyohei,
Nakada Masahisa
Publication year - 2019
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.201900178
Subject(s) - stereocenter , enantioselective synthesis , chemistry , michael reaction , thiourea , intramolecular force , organocatalysis , aldehyde , yield (engineering) , block (permutation group theory) , organic chemistry , benzoic acid , combinatorial chemistry , stereochemistry , catalysis , geometry , mathematics , materials science , metallurgy
The preparation of a chiral building block, including a stereodiad consisting of two tertiary stereogenic centers, by a highly enantioselective organocatalytic intramolecular Michael reaction is described. The use of a chiral secondary‐amine‐bearing thiourea substituted with a para ‐nitrophenyl group in the presence of benzoic acid is key to preparing the chiral building block in high yield and excellent enantioselectivity. The prepared chiral building block has both aldehyde and nitro groups, allowing a variety of functional‐group transformations necessary for the total synthesis of atisane‐type terpenoids.