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Asymmetric Construction of Bispiro‐Cyclopropane‐Pyrazolones via a [2+1] Cyclization Reaction by Dipeptide‐Based Phosphonium Salt Catalysis
Author(s) -
Lu Dongming,
Liu Xin,
Wu JiaHong,
Zhang Song,
Tan JianPing,
Yu Xiaojun,
Wang Tianli
Publication year - 2020
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.202000073
Subject(s) - pyrazolones , chemistry , cyclopropane , pyrazolone , phosphonium salt , catalysis , dipeptide , salt (chemistry) , phosphonium , combinatorial chemistry , organic chemistry , enantioselective synthesis , medicinal chemistry , ring (chemistry) , peptide , biochemistry
We reported herein an efficient alternative for asymmetric synthesis of structurally complicated chiral bispiro‐cyclopropane‐pyrazolones via dipeptide‐based phosphonium salt catalyzed [2+1] cyclization of 2,3‐dioxopyrrolidines and halogenated pyrazolones. With this catalytic asymmetric protocol, a broad range of bispiro heterocyclic compounds bearing a pyrazolone unit were prepared in high yields with excellent diastereo‐ and enatioselectivities. Of note, this transformation proceeds in a really short time under mild reaction conditions.