18531-96-9Relevant articles and documents
Synthesis and resolution of axially chiral C2-symmetric 1,1'-binaphthyl-substituted tetramethylethylenediamines
Mazaleyrat, Jean-Paul
, p. 2709 - 2721 (1997)
The axially chiral TMEDA derivatives 1 and 2 in which tetramethylethylenediamine is substituted respectively by one and two 1,1'-binaphthyl units at their 2,2'-positions, are of interest as chiral catalysts. Experimental details of their preparation in enantiomerically pure form are given. Two different routes have been followed, involving alkylation of both N,N-dimethyl ethylenediamine and ethylenediamine by 2,2'-bis-(bromomethyl)-1,1'-binaphthyl either enantiomerically pure as prepared from resolved 1,1'-binaphthyl-2,2'-dicarboxylic acid or racemic, the resulting racemic diamines 1 and 2 being then resolved with dibenzoyl-tartaric acid.
Facile synthesis of enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acid via lipase-catalyzed kinetic resolution
Furutani, Toshiyuki,Hatsuda, Masanori,Imashiro, Ritsuo,Seki, Masahiko
, p. 4763 - 4768 (1999)
Enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acids (R)-1 and (S)-1 have been synthesized through the lipase-catalyzed kinetic resolution of the racemic 2,2-bis(hydroxymethyl)-1,1'-binaphthyl (±)-2 and subsequent oxidation of the hydroxymethyl groups. (C) 2000 Elsevier Science Ltd.
Concise synthesis of binaphthol-derived chiral dicarboxylic acids
Egami, Hiromichi,Sato, Kentaro,Asada, Junshi,Kawato, Yuji,Hamashima, Yoshitaka
, p. 6384 - 6388 (2015)
Abstract 3,3'-Disubstituted 1,1'-binaphthyl-2,2'-dicarboxylic acids (1) were synthesized in three or four steps from commercially available BINOL via carbon dioxide fixation with organolithium to incorporate the carboxylic acid moieties, followed by either carboxylate-directed ortho-C-H arylation or Suzuki cross-coupling. This method provides easy access to various types of axiially chiral dicarboxylic acids, which should be useful for studies of chiral Br?nsted acid-catalyzed asymmetric reactions.
Stereoconservative cyanation of [1,1′-binaphthalene]-2,2′-dielectrophiles. An alternative approach to homochiral C2-symmetric [ 1,1′-binaphthalene]-2,2′-dicarbonitrile and its transformations
Kasak, Peter,Putala, Martin
, p. 729 - 740 (2000)
The performed study on the cyanation of [1,1′-binaphthalene]-2,2′-diiodide and [1,1′-binaphthalene]-2,2′-diyl ditriflate showed reactions with zinc cyanide catalyzed by palladium phosphane complex in DMF to be the most effective procedures with almost com
Double-Helical Oligo Esters: Chiral Twist of Two Aromatic Ester Chains
Nozaki, Kyoko,Terakawa, Takakiyo,Takaya, Hidemasa,Hiyama, Tamejiro
, p. 131 - 133 (1998)
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Embedding an allylmetal dimer in a chiral cavity: The unprecedented stereoselectivity of a twofold Wittig [1,2]-rearrangement
Schlosser, Manfred,Bailly, Frederic
, p. 16042 - 16043 (2006)
After α,α'-dimetalation, both 2,2′-diallyloxy-1,1′-binaphthyl and 2,2′-di-2-methylallyloxy-1,1′-binaphthyl undergo the Wittig rearrangement with perfect diastereoselectivity. When racemic 1,1′-binaphthyl-2,2′-diol ("BINOL") is used as the starting material, it gives rise to a 1:1 mixture of antipodal stereoisomers, whereas enantiomerically pure (M)-2,2′-diallyloxy-1,1′-binaphthyl affords (M)-(S,S)-1,1-(1,1′-binaphthyl-2,2′-diyl)bis(2-propen-1-ol) as the sole product. The (M)-(S,S)/(P)-(R,R) mixture resulting from the rearrangement of racemic 2,2′-diallyloxy-1,1′-binaphthyl can be effectively subjected to a kinetic racemate resolution by applying the Sharpless-Katsuki asymmetric epoxidation. The single-sided Wittig rearrangement of 2-allyloxy-2′-propyloxy-1,1′-binaphthyl proceeds without any diastereoselectivity as this substrate can only be monometalated and hence is incapable of intramolecular aggregate formation which is instrumental for the observed stereoselectivity. Copyright
A Practical Method for Optical Resolution of 1,1'-Binaphtyl-2,2'-dicarboxylic Acid via 1-Phenylethylamides
Oi, Shuichi,Matsuzaka, Yutaka,Yamashita, Junzo,Miyano, Sotaro
, p. 956 - 957 (1989)
Both enentiomers of 1,1'-binaphthyl-2,2'-dicarboxylic acid (100percent ee's by HPLC) were conveniently obtained in high yields (ca. 80percent of the theory) via fractional crystallization of the (S)-1-phenylethylamide diastereomers of the racemic acid followed by treatment with thionyl chloride and then alkaline hydrolysis
TRANSITION METAL COMPOUND FOR OLEFIN POLYMERIZATION CATALYST, OLEFIN POLYMERIZATION CATALYST COMPRISING SAME AND POLYOLEFIN POLYMERIZED USING SAME
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Paragraph 0050-0051, (2021/06/11)
Provided is a transition metal compound, represented by chemical formula 1, for an olefin polymerization catalyst. The details of chemical formula 1 are the same as those defined in the specification.