2015
DOI: 10.1002/anie.201504554
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Enantiospecific CH Activation Using Ruthenium Nanocatalysts

Abstract: The activation of C-H bonds has revolutionized modern synthetic chemistry. However, no general strategy for enantiospecific C-H activation has been developed to date. We herein report an enantiospecific C-H activation reaction followed by deuterium incorporation at stereogenic centers. Mechanistic studies suggest that the selectivity for the α-position of the directing heteroatom results from a four-membered dimetallacycle as the key intermediate. This work paves the way to novel molecular chemistry on nanopar… Show more

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Cited by 136 publications
(128 citation statements)
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References 45 publications
(86 reference statements)
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“…11 In the context of the nanoparticle surface chemistry, the theoretical calculations provide detailed information not only on the coordination mode of the species bound to the nanoparticle surface, 12 but also on the chemical reactions that may take place on these surfaces. 13 …”
Section: Introductionmentioning
confidence: 99%
“…11 In the context of the nanoparticle surface chemistry, the theoretical calculations provide detailed information not only on the coordination mode of the species bound to the nanoparticle surface, 12 but also on the chemical reactions that may take place on these surfaces. 13 …”
Section: Introductionmentioning
confidence: 99%
“…[3,7,8] Based on homogeneouso rh eterogeneous catalysis, numerousH IE methods have already been described. [1, 2, 4c, 9] Besides ongoing active research for C(sp 3 )ÀHa ctivation/deuteration, [10] particulara ttention has been paid to the selective ortho-directed HIE of aromatic substratesw ith commercial Crabtree's [11] and Kerr's catalyst. [12, 13] Some of the existing limitations with these classical HIE catalysts have recently been overcome by the introduction of anew generation of iridium catalysts containing bidentate ligandswith examples from Pfaltz [14] and Burgess.…”
mentioning
confidence: 99%
“…As exemplified in Scheme 3, treatment of d ‐ 5 a with 1,3‐dimethylbarbituric acid under the influence of tetrakis(tri‐2‐furylphosphine)palladium furnished N ‐unprotected amino ester d ‐ 1 a in good yield without loss of enantiomeric purity. In addition, benzyl ester d ‐ 1 a could be easily converted into d ‐phenylalanine via conventinal Pd‐catalyzed hydrogenation …”
Section: Methodsmentioning
confidence: 99%