Premium
Effective [3+1+1+1] Cycloaddition to Six‐Membered Carbocycle Based on DMSO as Dual Carbon Synthon
Author(s) -
Li Hui,
Su Miaodong,
Nie Zhiwen,
Yang Tonglin,
Luo Weiping,
Liu Qiang,
Guo Cancheng
Publication year - 2021
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.202100115
Subject(s) - chemistry , cycloaddition , synthon , cyclohexene , ketone , carbon skeleton , stereochemistry , carbon fibers , medicinal chemistry , organic chemistry , catalysis , materials science , composite number , composite material
A [3+1+1+1] cycloaddition was developed among 2‐arylpropene, ketone and DMSO in the presence of K 2 S 2 O 8 . 2‐arylpropene provides three carbons, ketone offers one carbon, and DMSO as dual carbon donor contributes two carbons to the six‐membered carbocycle. It gave the cyclohexene motif and spirocyclohexene skeleton. Four C−C bonds formed in this process. Both propylene and ketone could be well tolerated and give the corresponding cyclohexene or spirocyclohexene motif in useful yields. Based on the controlled experiments, a possible mechanism was proposed.