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Synthesis of Vinylcyclopropane‐Fused Pyrazolone Derivatives by Sulfur Ylide‐Initiated 1,6‐Michael Addition‐Cyclization Reactions
Author(s) -
Li Xiang,
Liu YanQing,
Kang JingWen,
Chen FeiYu,
He XiGuo,
Yuan ShanShan,
Guo Li,
Peng Cheng,
Huang Wei
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800710
Subject(s) - ylide , chemistry , pyrazolone , chemoselectivity , pyrazolones , cyclopropanation , michael reaction , enantioselective synthesis , combinatorial chemistry , sulfur , organic chemistry , catalysis
A highly diastereoselective cyclopropanation of α,β,γ,δ‐unsaturated pyrazolones has been disclosed. This method allows for construction of a vinylcyclopropane‐fused pyrazolone framework via a 1,6‐addition/substitution sequence providing excellent regio‐ and chemoselectivity, good yields, broad functional group tolerance and gram‐scale capacity. Moreover, the subsequent transformation of derivatives demonstrates great potential in building useful synthetic architectures.