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N,N‘-Ditosylhydrazine: A Convenient Reagent for Facile Synthesis of Diazoacetates†
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Section:Abstract
A novel entry to the synthesis of diazoacetates is disclosed. A variety of diazoacetates were synthesized from the corresponding bromoacetates by treatment with N,N‘-ditosylhydrazine in moderate to high yields. Ease of operation with the stable crystalline reagent as well as a short reaction time offer a useful alternative to the conventional methods.
Citing Articles
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This article has been cited by 6 ACS Journal articles (5 most recent appear below).
Synthesis of Substituted Pyrazoles via Tandem Cross-Coupling/Electrocyclization of Enol Triflates and Diazoacetates
David J. Babinski, Hector R. Aguilar, Raymond Still, and Doug E. FrantzThe Journal of Organic Chemistry2011 Article ASAPSynthesis of Substituted Pyrazoles via Tandem Cross-Coupling/Electrocyclization of Enol Triflates and Diazoacetates
David J. Babinski, Hector R. Aguilar, Raymond Still, and Doug E. FrantzThe Journal of Organic Chemistry2011 Article ASAPThe synthesis of 3,4,5-trisubstituted pyrazoles via a tandem catalytic cross-coupling/electrocyclization of enol triflates and diazoacetates is presented. The initial scope of this methodology is demonstrated on a range of differentially substituted ...
Polymerization of Various Alkyl Diazoacetates Initiated with (N-Heterocyclic Carbene)Pd/Borate Systems
Eiji Ihara, Hiroki Takahashi, Masaki Akazawa, Tomomichi Itoh, and Kenzo InoueMacromolecules2011 Article ASAPPolymerization of Various Alkyl Diazoacetates Initiated with (N-Heterocyclic Carbene)Pd/Borate Systems
Eiji Ihara, Hiroki Takahashi, Masaki Akazawa, Tomomichi Itoh, and Kenzo InoueMacromolecules2011 Article ASAP(NHC)Pd/borate initiating systems (NHC = N-heterocyclic carbene) were applied for polymerization of alkyl diazoacetates with a variety of ester groups. The monomers with n-hexyl, cyclohexyl, benzyl, and cholesteryl group as an ester group were transformed ...
Rh(II) Carbene-Promoted Activation of the Anomeric C−H Bond of Carbohydrates: A Stereospecific Entry toward α- and β-Ketopyranosides
Mélissa Boultadakis-Arapinis, Pascale Lemoine, Serge Turcaud, Laurent Micouin, and Thomas LecourtJournal of the American Chemical Society2010 132 (44), 15477-15479Rh(II) Carbene-Promoted Activation of the Anomeric C−H Bond of Carbohydrates: A Stereospecific Entry toward α- and β-Ketopyranosides
Mélissa Boultadakis-Arapinis, Pascale Lemoine, Serge Turcaud, Laurent Micouin, and Thomas LecourtJournal of the American Chemical Society2010 132 (44), 15477-15479In this communication we report a new strategy toward ketopyranosides based on a carbene-mediated activation of the anomeric C−H bond of carbohydrates. By forming a new carbon−carbon bond after a glycosylation step, this approach enables the preparation ...
Stereoselective Synthesis of (+)-Aspidofractinine
David Gagnon and Claude SpinoThe Journal of Organic Chemistry2009 74 (16), 6035-6041Stereoselective Synthesis of (+)-Aspidofractinine
David Gagnon and Claude SpinoThe Journal of Organic Chemistry2009 74 (16), 6035-6041We describe the synthesis of (+)-aspidofractinine, the enantiomer of a naturally occurring alkaloid of the kopsane family. Key features of the synthesis include a stereospecific cyanate to isocyanate rearrangement on a chiral scaffold, a ring-closing ...
Catalytic Homologation of Cycloalkanones with Substituted Diazomethanes. Mild and Efficient Single-Step Access to α-Tertiary and α-Quaternary Carbonyl Compounds
David C. Moebius and Jason S. KingsburyJournal of the American Chemical Society2009 131 (3), 878-879Catalytic Homologation of Cycloalkanones with Substituted Diazomethanes. Mild and Efficient Single-Step Access to α-Tertiary and α-Quaternary Carbonyl Compounds
David C. Moebius and Jason S. KingsburyJournal of the American Chemical Society2009 131 (3), 878-879Though volatile, toxic, and unstable, diazomethane is an indispensable one-carbon reagent with manifold uses in chemical synthesis. In this work, known protocols for hydrazone oxidation were adapted to permit facile access to a range of mono- and ...
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History
- Published In Issue August 02, 2007
- Received June 18, 2007
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