62717-50-4Relevant articles and documents
Synthesis and dopamine receptor pharmacological evaluations on ring C ortho halogenated 1-phenylbenzazepines
Alberts, Ian,Giri, Rajan,Harding, Wayne W.,Namballa, Hari K.,Sarker, Ananta
, (2020)
A series of 1-phenylbenzazepines containing bromine or chlorine substituents at the ortho position of the appended phenyl ring (2′-monosubstituted or 2′,6′- disubstituted patterns) were synthesized and evaluated for affinity towards dopamine D1
Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade
Franssen, Maurice C. R.,Hollmann, Frank,Martínez-Montero, Lía,Paul, Caroline E.,Süss, Philipp,Schallmey, Anett,Tischler, Dirk
, p. 5077 - 5085 (2021/08/16)
Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.
Enantiomer Separation of Nitriles and Epoxides by Crystallization with Chiral Organic Salts: Chirality Switching Modulated by Achiral Acids
Hirose, Takuji,Kodama, Koichi,Shimomura, Yuki
, p. 6552 - 6557 (2021/11/16)
Enantiomer separation of nitriles and epoxides by inclusion crystal formation with organic-salt type chiral hosts was achieved. The stereochemistry of the preferentially included nitrile could be switched only by changing the achiral carboxylic acid component. Crystallographic analysis of the inclusion crystals reveals that the hydrogen-bonding networks are controlled by the acidity of the phenol group of the acids, which results in chirality switching.
