218290-24-5

Usage

Reaction

Ligands for Mo catalyzed asymmetric allylic substitutions. Especially useful for the synthesis of tertiary and quaternary stereocenters. Exclusive license for this technology acquired by ChiroTech and is protected by pending Stanford University patents. Dynamic kinetic asymmetric formation of tertiary and quaternary stereogenic centers.

Upstream product

• 98-98-6 2-Picolinic acid 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 65-85-0 benzoic acid 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 29745-44-6 pyridine-2-carbonyl chloride 
• 2524-52-9 ethyl-2-picolinate 
• 201230-82-2 carbon monoxide 
• 57785-86-1 pyridin-2-yl tosylate 

Relevant academic research and scientific papers

Lanthanum(III) triflate catalyzed direct amidation of esters

Lanthanum trifluoromethanesulfonate is an effective single-component catalyst for synthesizing a variety of amides directly from esters and amines under mild conditions. Highly selective amidation of esters and amines, as well as catalyst-controlled amidation of esters, demonstrated the effectiveness of the catalyst system.

SYSTEM PROVIDING CONTROLLED DELIVERY OF GASEOUS CO FOR CARBONYLATION REACTIONS

A carbonylation system comprising at least one carbon monoxide producing chamber and at least one carbon monoxide consuming chamber forming an interconnected multi-chamber system, said interconnection allowing carbon monoxide to pass from the at least one carbon monoxide producing chamber to the at least one carbon monoxide consuming chamber, said at least one carbon monoxide producing chamber containing a reaction mixture comprising a carbon monoxide precursor and a catalyst, said at least one carbon monoxide consuming chamber being suitable for carbonylation reactions, said interconnected multi- chamber system being sealable from the surrounding atmosphere during carbonylation.

Ex situ generation of stoichiometric and substoichiometric 12CO and 13CO and its efficient incorporation in palladium catalyzed aminocarbonylations

A new technique for the ex situ generation of carbon monoxide (CO) and its efficient incorporation in palladium catalyzed carbonylation reactions was achieved using a simple sealed two-chamber system. The ex situ generation of CO was derived by a palladium catalyzed decarbonylation of tertiary acid chlorides using a catalyst originating from Pd(dba)2 and P(tBu)3. Preliminary studies using pivaloyl chloride as the CO-precursor provided an alternative approach for the aminocarbonylation of 2-pyridyl tosylate derivatives using only 1.5 equiv of CO. Further design of the acid chloride CO-precursor led to the development of a new solid, stable, and easy to handle source of CO for chemical transformations. The synthesis of this CO-precursor also provided an entry point for the late installment of an isotopically carbon-labeled acid chloride for the subsequent release of gaseous [ 13C]CO. In combination with studies aimed toward application of CO as the limiting reagent, this method provided highly efficient palladium catalyzed aminocarbonylations with CO-incorporations up to 96%. The ex situ generated CO and the two-chamber system were tested in the synthesis of several compounds of pharmaceutical interest and all of them were labeled as their [ 13C]carbonyl counterparts in good to excellent yields based on limiting CO. Finally, palladium catalyzed decarbonylation at room temperature also allowed for a successful double carbonylation. This new protocol provides a facile and clean source of gaseous CO, which is safely handled and stored. Furthermore, since the CO is generated ex situ, excellent functional group tolerance is secured in the carbonylation chamber. Finally, CO is only generated and released in minute amounts, hence, eliminating the need for specialized equipment such as CO-detectors and equipment for running high pressure reactions.

Chiral bis-pyridinium salts as novel stereoselective catalysts for the metal-free diels-alder cycloaddition of α,β-unsaturated aldehydes

The synthesis of enantiomerically pure C2-symmetric bis-pyridinium salts was realized through a simple condensation of 2-pyridyl-carboxyaldehydes with a chiral diamine. The catalytic properties of such novel compounds were preliminarily studied

New chiral diamide ligands: synthesis and application in allylic alkylation

A new family of chiral diamide ligands has been designed and synthesised. These ligands have been successfully applied to an asymmetric allylic substitution reaction. A palladium complex of one of the diamide ligands achieved enantioselectivities of up to 93% in the allylic alkylation of 1,3-diphenyl-3-acetoxyprop-1-ene.

The unusual role of CO transfer in molybdenum-catalyzed asymmetric alkylations

Spectroscopic and crystallographic studies were undertaken to gain insight into the mechanism of the highly regio- and enantioselective allylic aklylation reaction catalyzed by molybdenum. The chiral ligand (L*) consisting of the mixed benzamide/picolinam

N-cyclopentyl modulators of chemokine receptor activity

The present invention is directed to compounds of the formula I: (wherein R1, R3, R4, R5, R6, R7, R8, X, n, x and y are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.