622-30-0Relevant articles and documents
Direct conversion of chiral cyanohydrins to chiral nitrones by transimination
Hulsbos, Edith,Marcus, Jan,Brussee, Johannes,Van der Gen, Arne
, p. 1061 - 1067 (1997)
A new method for the preparation of enantiomerically pure N-benzyl nitrones is described. By using either a one-pot reduction-transimination or a one-pot Grignard addition-transimination sequence chiral O-protected α-hydroxynitriles can be converted into chiral aldo- and ketonitrones, respectively.
Chemoselective and Site-Selective Reductions Catalyzed by a Supramolecular Host and a Pyridine-Borane Cofactor
Morimoto, Mariko,Cao, Wendy,Bergman, Robert G.,Raymond, Kenneth N.,Toste, F. Dean
supporting information, p. 2108 - 2114 (2021/02/06)
Supramolecular catalysts emulate the mechanism of enzymes to achieve large rate accelerations and precise selectivity under mild and aqueous conditions. While significant strides have been made in the supramolecular host-promoted synthesis of small molecules, applications of this reactivity to chemoselective and site-selective modification of complex biomolecules remain virtually unexplored. We report here a supramolecular system where coencapsulation of pyridine-borane with a variety of molecules including enones, ketones, aldehydes, oximes, hydrazones, and imines effects efficient reductions under basic aqueous conditions. Upon subjecting unprotected lysine to the host-mediated reductive amination conditions, we observed excellent ?-selectivity, indicating that differential guest binding within the same molecule is possible without sacrificing reactivity. Inspired by the post-translational modification of complex biomolecules by enzymatic systems, we then applied this supramolecular reaction to the site-selective labeling of a single lysine residue in an 11-amino acid peptide chain and human insulin.
TRICYCLIC INHIBITORS OF HEPATITIS B VIRUS
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Page/Page column 54; 56, (2020/03/02)
The present invention relates to compounds that are inhibitors of hepatitis B virus (HBV). Compounds of this invention are useful alone or in combination with other agents for treating, ameliorating, preventing or curing HBV infection and related conditions. The present invention also relates to pharmaceutical compositions containing said compounds.
Chemoselective Synthesis of Amines from Ammonium Hydroxide and Hydroxylamine in Continuous Flow
Audubert, Clément,Bouchard, Alexanne,Mathieu, Gary,Lebel, Hélène
, p. 14203 - 14209 (2019/01/21)
The chemoselective amination of alkyl bromides and chlorides with aqueous ammonia and hydroxylamine was achieved in continuous flow to produce primary ammonium salts and hydroxylamines in high yields. An in-line workup was designed to isolate the corresponding primary amine, which was also telescoped in further reactions, such as acylation and Paal-Knorr pyrrole synthesis. Monosubstituted epoxides are also compatible with the reaction conditions.