109480-78-6Relevant articles and documents
Sn/Li exchange reactions in 1,ω-distannylated conjugated trienes and tetraenes: An enabling step for polyene synthesis
Burghart, Jochen,Brueckner, Reinhard
, p. 150 - 165 (2011)
Successive treatments of (1E,3E,5E)- or (1E,3Z,5E)-1,6-bis(tributylstannyl) hexa-1,3,5-triene with nBuLi and butanal rendered polyenyl alcohols resulting from one Sn/Li exchange reaction and exhibiting complete retention of the configuration of all C=C bonds. Mono- or dimethylated all-E-configured 1,6-distannylated conjugated trienes as well as all-E-1,8-bis(tributylstannyl) octa-1,3,5,7-tetraene and dimethylated congeners thereof reacted similarly. The respective Sn/Li exchange reactions affected the substructure Bu 3Sn-CH=CH with a 93-94:7-6 preference over Bu3Sn-CMe=CH and with a 90:10 preference over Bu3Sn-CH=CMe. all-E-1-Lithio-6- (tributylstannyl)hexa-1,3,5-triene was incorporated into navenone B after Negishi coupling and into (-)-cicutoxin after acylation. NMR spectroscopy of our navenone B specimen revealed that certain resonances were misassigned previously. Molecular tinkertoy: all-E-1,6-(Tributylstannyl)hexa-1,3,5-triene, all-E-1,8-(tributylstannyl)octa-1,3,5,7-tetraene, and related bis(tributylstannylated) polyenes undergomono-Sn/Li exchange reactions. They set the stage for terminus-differentiating functionalizations, which provide inter alianavenone B and (-)-cicutoxin.
Catalytic α-Deracemization of Ketones Enabled by Photoredox Deprotonation and Enantioselective Protonation
Zhang, Chenhao,Gao, Anthony Z.,Nie, Xin,Ye, Chen-Xi,Ivlev, Sergei I.,Chen, Shuming,Meggers, Eric
supporting information, p. 13393 - 13400 (2021/09/03)
This study reports the catalytic deracemization of ketones bearing stereocenters in the α-position in a single reaction via deprotonation, followed by enantioselective protonation. The principle of microscopic reversibility, which has previously rendered this strategy elusive, is overcome by a photoredox deprotonation through single electron transfer and subsequent hydrogen atom transfer (HAT). Specifically, the irradiation of racemic pyridylketones in the presence of a single photocatalyst and a tertiary amine provides nonracemic carbonyl compounds with up to 97% enantiomeric excess. The photocatalyst harvests the visible light, induces the redox process, and is responsible for the asymmetric induction, while the amine serves as a single electron donor, HAT reagent, and proton source. This conceptually simple light-driven strategy of coupling a photoredox deprotonation with a stereocontrolled protonation, in conjunction with an enrichment process, serves as a blueprint for other deracemizations of ubiquitous carbonyl compounds.
CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE
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Paragraph 000458; 000459, (2018/01/17)
Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.
Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides
Tona, Veronica,De La Torre, Aurélien,Padmanaban, Mohan,Ruider, Stefan,González, Leticia,Maulide, Nuno
supporting information, p. 8348 - 8351 (2016/07/26)
The synthesis of α-amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we present a stereoselective α-amination of amides employing simple azides that proceeds under mild conditions with release of nitrogen gas. The