Synthesis of Novel Enantiopure Fluorinated Building Blocks from Acyclic Chiral Allylsilanes

Tredwell, Matthew; Tenza, Kenny; Pacheco, M. Carmen; Gouverneur, Véronique

doi:10.1021/ol0518535

Cited by 45 publications

(23 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As expected,21 the presence of the remote stereogenic centre in 2 f did not induce stereocontrol upon fluorination and two diastereomers (1:1) were formed; these could be separated by silica gel chromatography.…”

Section: Resultssupporting

confidence: 77%

Effects of temperature and stress level on creep and tensile property of polypropylene sutures

Deng

Zhou

2003

J of Applied Polymer Sci

View full text Add to dashboard Cite

An investigation was conducted on creep behaviors of polypropylene sutures under different temperatures and stress levels in a temperature-controlled water bath. The study showed that temperature and stress level significantly affected the creep behaviors of the sutures. High temperature and stress level resulted in large creep and permanent deformation to the sutures. The creep data could be well described by an empirical formula. For most of the test conditions, the creep tests caused limited permanent deformation in sutures. Dependency of the permanent deformation on temperature may be illustrated by an Arrhenius-type equation. The tensile properties of the sutures were not adversely affected by a short-term creep test, indicating good mechanical performance for the polypropylene sutures. For the creep experiment of less than 3 h, the creep rupture of the sutures was observed at a stress level of 220 MPa and temperatures Ն 37°C.

show abstract

Section: Resultssupporting

confidence: 77%

Effects of temperature and stress level on creep and tensile property of polypropylene sutures

Deng

Zhou

2003

J of Applied Polymer Sci

View full text Add to dashboard Cite

show abstract

“…[35][36][37][38] Recently, catalytic fluorinations inclusive of asymmetric variants were developed using electrophilic fluorine sources. Electronrich p-systems such as metal enolates, 39 enamines, [40][41][42] various organosilanes [43][44][45] and indoles 46 have been investigated in this context.…”

Section: C(sp 3 )-F Bond Constructionmentioning

confidence: 99%

Transition metal catalysis and nucleophilic fluorination

2012

Self Cite

View full text Add to dashboard Cite

Transition metal catalyzed transformations using fluorinating reagents have been developed extensively for the preparation of synthetically valuable fluorinated targets. This is a topic of critical importance to facilitate laboratory and industrial chemical synthesis of fluorine containing pharmaceuticals and agrochemicals. Translation to (18)F-radiochemistry is also emerging as a vibrant research field because functional imaging based on Positron Emission Tomography (PET) is increasingly used for both diagnosis and pharmaceutical development. This review summarizes how fluoride sources have been used for the catalytic nucleophilic fluorination of various substrates inclusive of aryl triflates, alkynes, allylic halides, allylic esters, allylic trichloroacetimidates, benzylic halides, tertiary alkyl halides and epoxides. Until recently, progress in this field of research has been slow in part because of the challenges associated with the dual reactivity profile of fluoride (nucleophile or base). Despite these difficulties, some remarkable breakthroughs have emerged. This includes the demonstration that Pd(0)/Pd(II)-catalyzed nucleophilic fluorination to access fluoroarenes from aryl triflates is feasible, and the first examples of Tsuji-Trost allylic alkylation with fluoride using either allyl chlorides or allyl precursors bearing O-leaving groups. More recently, allylic fluorides were also made accessible under iridium catalysis. Another reaction, which has been greatly improved based on careful mechanistic work, is the catalytic asymmetric hydrofluorination of meso epoxides. Notably, each individual transition metal catalyzed nucleophilic fluorination reported to date employs a different F-reagent, an observation indicating that this area of research will benefit from a larger pool of nucleophilic fluoride sources. In this context, a striking recent development is the successful design, synthesis and applications of a fluoride-derived electrophilic late stage fluorination reagent. This new class of reagents could greatly benefit preclinical and clinical PET imaging.

show abstract

“…Homo-alkene-alkene CM of was described [1211,1212]. (224) Ruthenium catalyzed alkene-alkene CM of styrenes [1213], 1-allyl-tetrahydro-␤-carboline and -tetrahydroquinoline [1214], propenoic esters [1215,1216], alkenylsilanes [283,1217], allyl trimethylsilane [1218], conjugated dienes [1219,1220], allyl cyanide [1221], acrylonitrile [1222], ethenylazulene [1223], N-allylpyrimidines [1224], terminal 1-en-4-ols [644] and ␤-hydroxyenones [1225] with terminal alkenes were described.…”

Section: Metathesis Reactionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

View full text Add to dashboard Cite

Synthesis of Novel Enantiopure Fluorinated Building Blocks from Acyclic Chiral Allylsilanes

Cited by 45 publications

References 31 publications

Effects of temperature and stress level on creep and tensile property of polypropylene sutures

Effects of temperature and stress level on creep and tensile property of polypropylene sutures

Transition metal catalysis and nucleophilic fluorination

Transition metals in organic synthesis: Highlights for the year 2005

Contact Info

Product

Resources

About