The activation of C–H bonds in cycloalkanes by rhenium complexes

Baudry, Denise; Ephritikhine, Michel; Felkin, Hugh

doi:10.1039/c39820000606

Cited by 106 publications

(109 citation statements)

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“…Acid-catalyzed removal of the DMTr group led to 9-O-unprotected 42; immediate phosphorylation with dibenzyloxydiisopropylaminophosphane in the presence of tetrazole as a catalyst, followed by oxidation with tert-butylhydroperoxide afforded dibenzyl phosphate 43. The 2-O-allyl group was then removed with (1,5-cyclooctadiene)bis(methyldiphenylphosphane)iridium(I) hexafluorophosphate [27] as catalyst; subsequent cleavage of the generated enol ether with iodine in THF/water furnished 2-O-unprotected compound 44, which was transformed into diethyl phosphite 45 as described above.…”

Section: Eur J Org Chem 2000 1467ϫ1482 1468mentioning

confidence: 99%

Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

et al. 2000

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The reaction of sialyl phosphites 1, 22a‐d, 28, 39, and 45 with acyl‐protected riboside 5‐phosphorous acids 2a,b and 23 directly furnished, without addition of a catalyst, under phosphite/phosphate exchange the corresponding β‐configured sialyl riboside monophosphates 3a,b, 24a‐d, 29, 46, and 47. The synthesis of the starting materials, formation of the products, and their treatment with sodium methanolate in methanol and subsequent hydrolysis of the sialic acid ester moiety to provide the unprotected target molecules 4a,b, 25a‐d, 30, 48, and 49 is described. Investigations with α(2‐6)‐sialyltransferase from rat liver showed that base replacement in CMP‐Neu5Ac (4a,b) is not tolerated by the enzyme but that modifications of the 5‐, 8‐, or 9‐position of the neuraminic acid residue (25a‐d, 30, 48, 49) are tolerated.

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Section: Eur J Org Chem 2000 1467ϫ1482 1468mentioning

confidence: 99%

Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

et al. 2000

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“…[6] Removal of the acid-and base-stable allyl ether, which is preferably performed as the last deprotection, turned out to be a puzzling problem, since suitable reagents must not attack either the sulfur at C-1 or any functionality introduced in previous steps. The use of Baudry's catalyst [10] for isomerization of the allyl-to the 2-propenyl ether (which in turn can be cleaved by acidolysis) failed in a number of cases. Therefore, a reliable method for clean removal of the allyl ether on the solid phase had to be developed.…”

Section: Resultsmentioning

confidence: 98%

D‐Glucose as a Pentavalent Chiral Scaffold

et al. 2003

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“…This was extended to w-pentane which gave an r| 4 -trans-l,3-pentadiene complex. Rather remarkably, attempts to dislodge the coordinated diene with trimethyphosphite gave free 1-alkenes (a-olefms) (122). Selective conversion of «-alkane to 1-alkene was thus achieved, a reaction with great potential value if it could be effected catalytically in high yield.…”

Section: Alkane Dehydrogenationmentioning

confidence: 94%

Organometallic C—H Bond Activation: An Introduction

Goldman¹,

Goldberg²

2004

ACS Symposium Series

117

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An introduction to the field of activation and fimctionalization of C-H bonds by solution-phase transition -metal-based systems is presented, with an emphasis on the activation of aliphatic C-H bonds. The focus of this chapter is on stoichiometric and catalytic reactions that operate via organometallic mechanisms, i.e., those in which a bond is formed between the metal center and the carbon undergoing reactionThe carbon-hydrogen bond is the un-functional group. Its unique position in organic chemistry is well illustrated by the standard representation of organic molecules: the presence of C-H bonds is indicated simply by the absence of any other bond. This "invisibility" of C-H bonds reflects both their ubiquitous nature and their lack of reactivity. With these characteristics in mind it is clear that if the ability to selectively fiinctionalize C-H bonds were well developed, it could potentially constitute the most broadly applicable and powerful class of transformations in organic synthesis. Realization of such potential could revolutionize the synthesis of organic molecules ranging in complexity from methanol to the most elaborate natural or unnatural products.The following chapters in this volume offer a view of many of the current leading research efforts in this field, in particular those focused on the activation

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The activation of C–H bonds in cycloalkanes by rhenium complexes

Cited by 106 publications

References 0 publications

Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

D‐Glucose as a Pentavalent Chiral Scaffold

Organometallic C—H Bond Activation: An Introduction

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