15753-89-6Relevant academic research and scientific papers
Difluoro- and trifluoro diazoalkanes-complementary approaches in batch and flow and their application in cycloaddition reactions
Hock, Katharina J.,Mertens, Lucas,Metze, Friederike K.,Schmittmann, Clemens,Koenigs, Rene M.
, p. 905 - 909 (2017/08/14)
Herein we report on applications of fluorinated diazoalkanes in cycloaddition reactions, with the emphasis on studying subtle differences between diverse fluorinated diazo compounds. These differences led to two major synthetic protocols in batch and flow that allow the safe and scalable synthesis of fluoroalkyl-, sulfone-substituted pyrazolines.
DABSO-based, three-component, one-pot sulfone synthesis
Deeming, Alex S.,Russell, Claire J.,Hennessy, Alan J.,Willis, Michael C.
supporting information, p. 150 - 153 (2014/01/23)
The addition of Grignard reagents or organolithium reagents to the SO 2-surrogate DABSO generates a diverse set of metal sulfinates, suitable for direct conversion to sulfone products. The metal sulfinates can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums.
The epoxy-Ramberg-Baecklund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols
Evans, Paul,Johnson, Paul,Taylor, Richard J. K.
, p. 1740 - 1754 (2007/10/03)
The epoxy-Ramberg-Baecklund reaction (ERBR) is outlined, in which α,β-epoxy sulfones are converted into a range of mono-, di- and tri-substituted allylic alcohols, on treatment with base. Modification of this method enabled the preparation of enantio-enriched allylic alcohols following the diastereoselective epoxidation of enantio-enriched vinyl sulfones that were accessed efficiently from the chiral pool. The scope, optimisation and limitations of the ERBR as a method for the preparation of allylic alcohols are discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
N-H insertion reactions of rhodium carbenoids. Part 3. The development of a modified Bischler indole synthesis and a new protecting-group strategy for indoles
Bashford, Katherine E.,Cooper, Anthony L.,Kane, Peter D.,Moody, Christopher J.,Muthusamy, Sendogagounder,Swanna, Elizabeth
, p. 1672 - 1687 (2007/10/03)
A modified version of the Bischler indole synthesis has been developed in which the key step is the N-H insertion reaction of rhodium carbene intermediates derived from α-diazo-β-ketoesters with anilines. Thus N-methylanilines 1 react with diazoketoesters 2 in the presence of dirhodium(II) acetate to give (N-arylamino)ketones 3, cyclisation of which using boron trifluoride-ethyl acetate or acidic ion exchange resin gives the indoles 4. In order to extend this method to the synthesis of N-unsubstituted indoles, a new protecting group strategy for indoles was developed. In this, anilines are reacted with α,β-unsaturated-esters or -sulfones to give the conjugate addition products 6 and 9, cyclisation of which gives indoles 8 and 11. The N-(2-ethoxycarbonylethyl)- and -(2-sulfonylethyl)- protecting groups are readily removed from indoles 8 and 11 by treatment with base.
The Epoxy-Ramberg-Backlund reaction: A new route to allylic alcohols
Evans, Paul,Taylor, Richard J. K.
, p. 3055 - 3058 (2007/10/03)
A new variant of the Ramberg-Backlund reaction is described, the epoxy-Ramberg-Backlund reaction (ERBR), in which α,β-epoxysulfones, on treatment with base, are converted into a range of mono-, di- and tri-substituted allylic alcohols. The scope and limitations of the ERBR are discussed.
CYCLIZATION OF SELECTED BENZYL SULFONE DERIVATIVES UNDER PHASE TRANSFER CATALYTIC CONDITIONS
El-Zohry, Maher F.,El-Khawaga, Ahmed M.,Abdel-Wahab, Aboel-Magd A.
, p. 149 - 152 (2007/10/02)
Seven selected benzyl chloroalkyl sulfones (1a-c) and benzyl carboethoxyalkyl sulfones (1d-g) has been subjected to treatment with aqueous NaOH (50percent) under PTC conditions.Analysis of the product mixtures revealed competitive cyclization, elimination
