102555-71-5Relevant articles and documents
Synthesis of chiral 3,3′-disubstituted 1,1′-binaphthyl-2, 2′-disulfonic acids
Hatano, Manabu,Sugiura, Yoshihiro,Ishihara, Kazuaki
, p. 1311 - 1314 (2010)
A convenient synthesis of chiral 3,3′-disubstituted 1,1′-binaphthyl-2,2′-disulfonic acids (BINSA, 1) was developed. The key was directed ortho-lithiation of BINSA methyl ester 2 with n-BuLi and subsequent reaction with an electrophile. Electrophiles such as Br2, I2, Me3SiOTf, and i-PrOB(Pin) reacted smoothly with 3,3′-dilithiated BINSA methyl ester, and the corresponding 3,3′-dihalo-, 3,3′-bis(trimethylsilyl)-, and 3,3′-diboryl- BINSA derivatives were obtained in yields of 21-78%. This simple synthetic method is highly attractive since the ability to prepare 3,3′- disubstituted BINOLs in advance can be useful.
A useful sulfur-transfer reaction with tetrathiomolybdate: Conversion of arylamines to aryl disulfides
Bhar,Chandrasekaran
, p. 785 - 786 (1994)
A convenient method for the synthesis of a series of symmetrical aryl disulfides from arylamines via the reaction of their stable diazonium salts with tetrathiomolybdate under anhydrous conditions is described.
ASYMMETRIC OXIDATION OF THIOETHERS. OPTICAL RESOLUTION OF -2,2'-DITHIOL
Furia, Fulvio Di,Licini, Giulia,Modena, Giorgio,Lucchi, Ottorino De
, p. 2575 - 2576 (1989)
Almost optically pure (e.e.>98percent) -2,2'-dithiol (2) is obtained by resolution of racemic 2 via the transformation of the sulfidryl functions into the corresponding thioethers 3 which are asymmetrically oxidized to diastereomeric chiral monosulfoxides 4 and then reconverted into 2.The diastereo and enantioselectivity is dependent on the structure of the thioether; i.e. the dimethylthioether 3a gives two diastereomeric sulfoxides 4a in ca. 1:1 ratio, each of them in >98percent e.e., while cyclic dithioethers 3b-d afford a single diastereomeric sulfoxide 4b-d in 46-78percent e.e..
Conformational polymorphism and thermorearrangement of 2,2′-bis-O-(N,N-dimethylthiocarbamato)-1,1′-binaphthalene. A facile synthesis of 1,1′-binaphthalene-2,2′-dithiol
Bandarage, Upul K.,Simpson, Jim,Smith, Robin A. J.,Weavers, Rex T.
, p. 3463 - 3472 (1994)
The title compound was found to exhibit conformational polymorphism which greatly influenced the efficiency of the thermorearrangement to 2,2′-bis-S-(N,N-dimethylthiocarbamato)-1,1′-binaphthalene. Recognition of this phenomenon has allowed a reproducible synthesis of 1,1′-binaphthalene-2,2′ dithiol.
Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol
Brégent, Thibaud,Bouillon, Jean-Philippe,Poisson, Thomas
supporting information, p. 13966 - 13970 (2021/08/25)
The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.
Practical synthetic approach to chiral sulfonimides (CSIs) - Chiral bronsted acids for organocatalysis
He, Hao,Chen, Ling-Yan,Wong, Wai-Yeung,Chan, Wing-Hong,Lee, Albert W. M.
supporting information; experimental part, p. 4181 - 4184 (2010/10/02)
A general approach to the synthesis of optically pure 3,3'diaryl chiral sulfonimides (CSIs) from racemic BINOL has been developed. ortho-Lithiation is directed by the sulfonyl groups, and the resulting dihalides serve as the common precursors for the aryl-substituted CSIs.
