1246396-62-2

Upstream product

• 204519-27-7 N-acetyl-3-amino-1H-indene 
• 100-42-5 styrene 
• 600-00-0 ethyl 2-bromoisobutyrate 
• 1246396-63-3 ethyl 4-[(tert-butylsulfinyl)amino]-2,2-dimethyl-4-phenylbutanoate 

Downstream Products

• 1246394-16-0 (7S)-2-[(3,3-dimethyl-2-oxo-5-phenylpyrrolidin-1-yl)methyl]-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 

Relevant academic research and scientific papers

Copper-Catalyzed Three-Component Alkene Carbofunctionalization: C-N, C-O, and C-C Bond Formation from a Single Reaction Platform

A general system achieving three-component intermolecular carbofunctionalization of alkenes is presented, including carboetherification, carboesterification, carboarylation, and carboamination. The scope of the reaction is presented with respect to the carbon electrophile, the olefin, and the nucleophile. Furthermore, the synthesis of δ-lactams via a carboamination reaction is demonstrated in a telescoped three-step protocol.

Palladium-catalyzed cross-coupling of enamides with sterically hindered α-bromocarbonyls

Palladium-catalyzed intermolecular alkylation of enamides with α-bromo carbonyls was developed. Under mild reaction conditions, various cyclic and acyclic enamides reacted well with α-bromo carbonyls to afford the corresponding multi-substituted alkene pr

Harnessing Secondary Coordination Sphere Interactions That Enable the Selective Amidation of Benzylic C-H Bonds

Engineering site-selectivity is highly desirable especially in C-H functionalization reactions. We report a new catalyst platform that is highly selective for the amidation of benzylic C-H bonds controlled by π-πinteractions in the secondary coordination sphere. Mechanistic understanding of the previously developed iridium catalysts that showed poor regioselectivity gave rise to the recognition that the π-cloud of an aromatic fragment on the substrate can act as a formal directing group through an attractive noncovalent interaction with the bidentate ligand of the catalyst. On the basis of this mechanism-driven strategy, we developed a cationic (ν5-C5H5)Ru(II) catalyst with a neutral polypyridyl ligand to obtain record-setting benzylic selectivity in an intramolecular C-H lactamization in the presence of tertiary C-H bonds at the same distance. Experimental and computational techniques were integrated to identify the origin of this unprecedented benzylic selectivity, and robust linear free energy relationship between solvent polarity index and the measured site-selectivity was found to clearly corroborate that the solvophobic effect drives the selectivity. Generality of the reaction scope and applicability toward versatile γ-lactam synthesis were demonstrated.

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts

Intramolecular insertion of met al nitrenes into carbon-hydrogen bonds to form γ-lactam rings has traditionally been hindered by competing isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding γ-lactams via sp3 and sp2 C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules.

CGRP RECEPTOR ANTAGONISTS

Compounds of Formula (I) (wherein variables A1, A2, A3, ring-B, m, n, J, E1, E2, E3, R5, RPG and Y are as described herein), which are useful as antagonists of CGRP receptors, an