772-15-6Relevant articles and documents
Asymmetric conjugate addition reactions with chiral oxadiazinones: Unusual conformational properties of the oxadiazinones
Obe, Fatima Olayemi,Davis, Ryan A.,Spurlock, Jennifer,Grunloh Barnes, Morgan M.,Lindvall, Tyler,Wendorf, Micah S.,Delach, Christina,Ferrence, Gregory M.,Standard, Jean M.,Hitchcock, Shawn R.
, (2021/02/26)
A series of Ephedra based oxadiazinones have been prepared, acylated, and examined in the asymmetric conjugate addition reaction with Grignard reagents in the presence of copper(I) bromide-dimethyl sulfide complex. The highest diastereoselectivity that was obtained in the conjugate addition reaction was observed with the (1R,2S)-ephedrine based N4-methyloxadiazinone (5:1 d.r.) favoring the formation of the (S)-configuration of the conjugate addition product. Efforts to enhance the level of diastereoselection via increasing the steric volume of the stereo-directing N4-substituent of the oxadiazinone (N4- = p-methoxyphenyl or -isopropyl) led to an observed decrease in the level of diastereoselection. A computational study was conducted to examine the conformations adopted by the N4-methyloxadiazinone vs. the N4-isopropyl-oxadiazinone that yielded the lower diastereoselectivity. An argument is made for the stereoelectronic properties of the N4-substituent being the cause of both the moderate diastereoselectivity and the unexpected facial preference for the conjugate addition.
CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids
Link, Achim,Zhou, Yujing,Buchwald, Stephen L.
, p. 5666 - 5670 (2020/07/24)
The direct enantioselective copper hydride (CuH)-catalyzed synthesis of β-chiral amides from α,β-unsaturated carboxylic acids and secondary amines under mild reaction conditions is reported. The method utilizes readily accessible carboxylic acids and tolerates a variety of functional groups in the β-position including several heteroarenes. A subsequent iridium-catalyzed reduction to γ-chiral amines can be performed in the same flask without purification of the intermediate amides.
OPIOID RECEPTOR MODULATORS AND PRODUCTS AND METHODS RELATED THERETO
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, (2019/10/29)
Compounds are provided having the structure of Formula (I): or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein A, B, L, R3, R4, R5, R6, R8, m and n are as defined herein. Such compounds modulate the opioid receptor, particulare the mu-opioid receptor (MOR) and/or the kappa-opioid receptor (KOR), and/or the delta-opioid receptor (DOR). Products containing such compounds, as well as methods for their use and preparation, are also provided.
