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Enantioselective Michael Addition Reactions to Construct SCF 3 ‐containing Stereocenter Catalyzed by Chiral Quaternary Phosphonium Salts
Author(s) -
Hong Haoran,
Zheng Changwu,
Zhao Gang,
Shang Yongjia
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.202001026
Subject(s) - stereocenter , enantioselective synthesis , chemistry , electronegativity , catalysis , phosphonium , michael reaction , lipophilicity , stereochemistry , organic chemistry , medicinal chemistry , combinatorial chemistry
Abstract The trifluoromethylthio group is significant in drug design for its high stability, electronegativity, and lipophilicity. Herein, a series of indenone structures containing the SCF 3 group and an adjacent chiral quaternary stereocenter were synthesized by an asymmetric Michael addition reaction using an ion pair catalyst derived from amino acids. The desired products were obtained in excellent yields (up to 98%) and good to high stereoselectivities (up to 97% ee and >20:1 dr).