Premium
Asymmetric Synthesis of Cyclohexane‐Fused Drug‐Like Spirocyclic Scaffolds Containing Six Contiguous Stereogenic Centers via Organocatalytic Cascade Reactions
Author(s) -
Han Bo,
Huang Wei,
Ren Wen,
He Gu,
Wang Jinhui,
Peng Cheng
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400764
Subject(s) - stereocenter , chemistry , cyclohexanes , cascade reaction , rhodanine , stereoselectivity , stereochemistry , combinatorial chemistry , cyclohexane , michael reaction , tandem , yield (engineering) , aldol reaction , enantioselective synthesis , organic chemistry , catalysis , materials science , metallurgy , composite material
Drug‐like spirocyclic scaffolds have been prepared asymmetrically by fusing fully functionalized cyclohexanes with medicinally important pyrazolone, rhodanine, barbituric acid or indandione moieties. This approach utilizes an organocatalytic tandem Michael–Michael–aldol reaction that yields diverse chiral spirocyclic backbones containing six contiguous stereogenic centers and multiple functional groups. The target compounds are generated in good yield and with high stereoselectivity (up to 99 % ee and 95:5 dr ). Intriguingly, diastereocontrol of the spiro‐products changes depending on the substrate.