791616-64-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3,3'-Dibromo-5,5',6,6',7,7',8,8'-octahydro-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene is used as a chiral ligand for the synthesis of enantiomerically pure pharmaceutical compounds. Its high enantioselectivity ensures the production of the desired enantiomer, which is crucial for the efficacy and safety of many drugs, as different enantiomers can have different biological activities.
Used in Chemical Synthesis:
In the field of chemical synthesis, (R)-3,3'-Dibromo-5,5',6,6',7,7',8,8'-octahydro-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene is used as a catalyst for various reactions, including asymmetric hydrogenation, hydroformylation, and cyclopropanation. Its unique molecular structure allows it to facilitate these chemical transformations with high efficiency and selectivity, making it an indispensable tool for creating complex molecules and compounds.
Used in Research and Development:
(R)-3,3'-Dibromo-5,5',6,6',7,7',8,8'-octahydro-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene is also utilized in research and development settings. Its ability to catalyze a wide range of reactions and its easily modifiable functional groups make it an attractive candidate for exploring new reaction pathways and developing novel synthetic methods. (R)-3,3'-Dibromo-5,5',6,6',7,7',8,8'-octahydro-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene contributes to the advancement of chemical knowledge and the discovery of new materials and compounds with potential applications in various industries.

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 39648-74-3 (Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol 
• 13057-17-5 bromethyl methyl ether 

Relevant academic research and scientific papers

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

Enantioselective organocatalytic fluorination-induced Wagner-Meerwein rearrangement

Cracked under strain: Strained allylic cyclobutanols and cyclopropanols readily undergo a ring expansion described by the title rearrangement. This reaction is promoted by catalytic amounts of 1 and displays high tolerance with respect to the substrate scope. The corresponding β-fluoro spiroketone products are isolated in high yields and with excellent stereoselectivities. EDG=electron-donating group, EWG=electron-withdrawing group. Copyright

CATALYSTS FOR METATHESIS REACTIONS INCLUDING ENANTIOSELECTIVE OLEFIN METATHESIS, AND RELATED METHODS

The present invention provides compositions comprising metal complexes, and related methods. In some embodiments, metal complexes of the invention may be useful as catalysts for chemical reactions, including metathesis reactions, wherein the catalysts exhibit enhanced activity and stereoselectivity. In some embodiments, the invention may advantageously provide metal complexes comprising a stereogenic metal atom. Such metal complexes may be useful in enantioselective catalysis.

Design and stereoselective preparation of a new class of chiral olefin metathesis catalysts and application to enantioselective synthesis of quebrachamine: catalyst development inspired by natural product synthesis

A total synthesis of the Aspidosperma alkaloid quebrachamine in racemic form is first described. A key catalytic ring-closing metathesis of an achiral triene is used to establish the all-carbon quaternary stereogeniccenter and the tetracyclic structure of the natural product; the cataly tic transformation proceeds with reasonable efficiency through the use of existing achiral Ru or Mo catalysts. Ru- or Mo-based chiral olefin metathesis catalysts have proven to be inefficient and entirely nonselective in cases where the desired product is observed. In the present study, the synthesis route thus serves as a platform for the discovery of new olefin metathesis catalysts that allow for efficient completion of an enantioselective synthesis of quebrachamine. Accordingly, on the basis of mechanistic principles, stereogenic-at-Mo complexes bearing only monodentate ligands have been designed. The new catalysts provide significantly higher levels of activity than observed with the previously reported Ru-or Mo-based complexes. Enantiomerically enriched chiral alkylidenes are generated through diastereoselective reactions involving achiral Mo-bas ed bispyrrolides and enantiomerically pure silyl-protected binaphthols. Such chiral catalysts initiate the key enantioselective ring-closing metathesis step in the total synthesis of quebrachamine efficiently (1 mol percent loading, 22 °C, 1h, >98percent conversion, 84percent yield) and with high selectivity (98:2 er, 96percent ee).

ASYMMETRIC-SYNTHESIS CATALYST BASED ON CHIRAL BROENSTED ACID AND METHOD OF ASYMMETRIC SYNTHESIS WITH THE CATALYST

A compound usable as an asymmetric synthesis catalyst which can be easily synthesized without using any metal such as a lanthanoid group element; a method of asymmetric synthesis with the compound; and a chiral compound obtained by the asymmetric synthesis method. A Broensted acid is used as a catalyst in asymmetric synthesis, the chiral Broensted acid being represented by formula (1) below or formula (3) below. The asymmetric synthesis method employs the catalyst. Asymmetric synthesis with the catalyst gives a chiral compound.