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Synthetic Method for 2,2'‐Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono‐Phosphoric Acid Catalyst
Author(s) -
Momiyama Norie,
Okamoto Hiroshi,
Shimizu Masahiro,
Terada Masahiro
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22429
Subject(s) - chemistry , catalysis , phosphoric acid , chirality (physics) , enantioselective synthesis , organic chemistry , brønsted–lowry acid–base theory , combinatorial chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
A practical synthetic method for 2,2'‐disubstituted fluorinated binaphthyl derivatives was achieved using magnesium bis(2,2,6,6‐tetramethylpiperamide) [Mg(TMP) 2 ], prepared from LiTMP (2 equiv) and MgBr 2 (1 equiv), which allows for access to a variety of fluorinated binaphthyl compounds. The utility of the fluorinated binaphthyl backbone was evaluated in F 10 BINOL derived chiral mono‐phosphoric acid ( R )‐ 19 as the chiral Brønsted acid catalyst. The catalyst ( R )‐ 19 performs exceptionally well in the catalytic enantioselective imino‐ene reaction, demonstrating the potential of a fluorinated binaphthyl framework. Chirality 27:464–475, 2015. © 2015 Wiley Periodicals, Inc.