86457-66-1

Upstream product

• 18531-96-9 1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 18531-96-9 (S)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 

Downstream Products

• 173847-46-6 2,2'-bis<(N-3-bromophenyl-N-methyl)aminocarbonyl>-1,1'-binaphthyl 
• 173847-47-7 2,2'-bis<(N-3-bromophenyl-N-methyl)aminomethyl>-1,1'-binaphthyl 
• 1202936-49-9 C₂₀H₁₂(CONH(C₆H₃(C₂H₅)2))2 
• 1202936-51-3 C₂₀H₁₂(CONH(C₆H₃(CH(CH₃)2)2))2 
• 1202936-47-7 C₂₀H₁₂(CONH(C₆H₂(CH₃)3))2 
• 136880-28-9 [1,1']Binaphthalenyl-2,2'-dicarboxylic acid bis-phenylamide 
• 18531-96-9 (S)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 138092-98-5 (S)-2,2'-dibenzoyl-1,1'-binaphthyl 
• 746-46-3 (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid 

Relevant academic research and scientific papers

Enantiopure isoplagiochin C by directed deracemization through axis-to-axis chirality transfer

Isoplagiochin C 1 was prepared for the first time in enantiopure form from synthetic racemic material, using a novel stereochemical concept. This macrocyclic bisbibenzyl contains two biaryl axes. Of these, axis A is configurationally stable by its fixation within the macrocyclic framework, while axis B is stereochemically unstable. By diesterification of rac-1 with enantiopure (P)-1,1′-binaphthyl-2,2′-dicarboxylic acid, axis B is locked in its P-configuration, thus allowing the resolution and separate saponification of dilactones (PA,PB,P)-3 and (M A,PB,P)-3 to give the pure enantiomers of 1. This concept permits recycling of any undesired enantiomer of 1 by thermal equilibration of the respective diastereomer of 3.

C2-symmetric zirconium Bis(Amidate) complexes with enhanced reactivity in aminoalkene hydroamination

Binaphthalenedicarboxamide zirconium complexes exhibit significantly enhanced catalytic activity in aminoalkene hydroamination reactions with respect to substrate scope (substrates without gem-dialkyl activation; cyclization of aminoheptenes), catalyst loading (as low as 0.5 mol %) and reaction temperatures (as low as 70 °C) compared to previous group 4 metal-based hydroamination catalyst systems.

A designer axially chiral amino sulfonamide as an efficient organocatalyst for direct asymmetric anti/-selective mannich reactions and syw-selective cross-aldol reactions

A direct asymmetric Mannich reaction using a novel axially chiral amino sulfonamide (S)-3 that is highly anti- and enantioselective has been developed. For instance, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and a-imino esters proceeded smoothly to give anti Mannich products with a significantly higher antilsyn ratio and enantioselectivity than previously possible. By utilizing N-Boc-protected aro-matic imines instead of a-imino esters, the synthetically useful Boc protecting group and various aromatic or heteroaromatic substituents were installed into the anti Mannich products and consequently the substrate scope of the anri'-selective Mannich reaction and the synthetic utility of the anti Mannich products have been expanded. The axially chiral amino sulfonamide (S)-3 has also been successfully applied to asymmetric direct cross-aldol reaction between two different aldehydes. The catalyst (S)-3 has the advantage of giving mainly syn products, whereas proline shows the opposite anti selectivity.

Design of an axially chiral amino acid with a binaphthyl backbone as an organocatalyst for a direct asymmetric aldol reaction

(Chemical Equation Presented) A robust binaphthyl-based amino acid ((S)-1) exhibits higher stability and selectivity than proline for the catalysis of a direct asymmetric aldol reaction between aldehydes and acetone (see scheme; DMF = N,N-dimethylformamid

New, improved procedure for the synthesis of structurally diverse N-spiro C2-symmetric chiral quaternary ammonium bromides

Selective, direct ortho magnesiation of (S)-2,2′bis(isopropoxycarbonyl)-1,1′-binaphthyl (6) has been achieved under mild conditions, using magnesium bis(2,2,6,6-tetramethylpiperamide) [Mg(TMP)2]. In combination with the subsequent reaction with

Long-distance propagation of stereochemical information by stereoselective synthesis of copper(i) bipyridine helicates

Several chiral ligands have been obtained by linking two achiral chains containing up to three bipyridine units to various dissymmetric templates. Addition of copper(I) and silver(I) ions resulted in the highly stereoselective formation of bis(helicates), the absolute configuration of which was dictated by that of the templates, with (P) or (M) helicates being formed from (R) or (S) templates, respectively. In the cases of ligands containing three bipyridine units, the stereochemical information was transferred from the templates to the helicates over a distance of about 20 ?.

Design and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins

A series of C2 symmetric chiral ketones were designed and synthesized for catalytic asymmetric epoxidation of unfunctionalized olefins. Among those ketones screened, (R)-7, (R)-9, and (R)-10 were found to be highly efficient catalysts for epoxidation of trans-stilbenes with enantioselectivities in the range of 84-95%. Convincing evidence was provided for a spiro transition state of dioxirane epoxidation. Through the 18O-labeling experiment, chiral dioxiranes were found to be the intermediates in chiral ketone catalyzed epoxidation reactions.

Cyclic polyamides consisting of 1,1'-binaphthyls. 'Chiral twist' of glycine residues

Two cyclic polyamides were prepared from glycine and 1,1'-binaphthyls, and their structures have been determined by single-crystal X-ray analysis. Local conformations of glycines are twisted when they are sandwiched between two (R)-1,1'-bioaphthyls. Glycines are stretched into planer conformations when they are placed between an (R)1,1'-binaphthyl and an (S)-1,1'- binaphthyl. Conformations of these two cyclic polyamides in organic solvents and their interaction with other organic molecules are also discussed.

Homochiral 2,2'-bis(oxazolyl)-1,1'-binaphthyls as ligands for copper(I)- catalyzed asymmetric cyclopropanation

Homochiral 2,2'-bis[4-(alkyl)oxazol-2-yl]-1,1'-binaphthyls, which possess both binaphthyl axial chirality and carbon centred chirality, were prepared from 1,1'-binaphthyl-2,2'-dicarboxylic acid and 2-alkyl-2-aminoethanols in high yields. Asymmetric cyclopropanation of styrene with diazoacetates in the presence of 2 mol % of copper(I) triflate and (S)-2,2'-bis[(S)-4-(t- butyl)oxazol-2-yl]-1,1'-binaphthyl gave optically active 2- (phenyl)cyclopropane-carboxylates of up to 97% ee.

Does diatomic sulfur (S2) react as a free species?

A detailed study into the design and synthesis of stable 1,2-dithietane derivatives for the generation of diatomic sulfur (S2) was undertaken. Computer-aided evaluation of enthalpic differences was used to direct the synthesis of target compounds and, although all of the compounds calculated to afford S2 that were prepared did yield diatomic sulfur, an isolable 1,2-dithietane other than dithiatopazine failed to materialize. The results of this study provide convincing evidence that the computational procedure outlined can be successfully used to predict the course of S2 extrusion pathways from potential dithionocarbonylated derivatives. To determine if the disulfide moiety found in the Diels-Alder adduct derived from the addition of diatomic sulfur to conjugated 1,3-dienes is due to a transference mechanism involving the transient 1,2-dithietane intermediate, a chiral nonracemic binaphthyl source of S2 was prepared. Reactions of S2 from this source with chiral nonracemic and prochiral conjugated 1,3-dienes indicate that the added disulfide moiety would be inconsistent with a transference mechanism and that a "free" acting S2 unit is more likely to be involved.