156298-68-9Relevant academic research and scientific papers
N,N′-ditosylhydrazine: A convenient reagent for facile synthesis of diazoacetates
Torna, Tatsuya,Shimokawa, Jun,Fukuyama, Tohru
, p. 3195 - 3197 (2008/02/10)
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.
63. Enantioselective Formation of Bicyclic Lactones by Rhodium-Catalyzed Intramolecular CH-Insertion Reactions
Mueller, Paul,Polleux, Philippe
, p. 645 - 654 (2007/10/02)
The decomposition of cyclohexyl diazoacetate (5a) in the presence of the chiral 4> catalyst leads to a 3:1 cis/trans mixture of bicyclic lactone 6a with an enantiomeric excess of 95-97percent (cis) and 90percent (trans).The conformationally rigid tert-butyl derivatives 5b and 5c afford, in the presence of the same catalyst, 6b and 6c, respectively, via insertion into the equatorial C-H bonds exclusively, with ee's of ca. 95percent.A remarkable degree of induction (92-95percent) results in the lactone 6g upon decomposition of 1-isopropyl-2-methylpropyl diazoacetate (5g).The diazoacetates derived from 1-methylcyclohexanol, cyclopentanol and 1-methylcyclopentanol (5d-f) afford under similar conditions insertion products with higher diastereoselectivity, but significantly lower enantioselectivity.Other dirhodium catalysts are less efficient.
