936632-16-5Relevant academic research and scientific papers
Enantioselective Iodine(III)-Mediated Synthesis of α-Tosyloxy Ketones: Breaking the Selectivity Barrier
Basdevant, Benoit,Legault, Claude Y.
, p. 4918 - 4921 (2015/10/12)
The development of practical methods to access chiral nonracemic α-substituted ketones is of particular importance due to their ubiquitous nature. Unprecedented levels of enantioselectivity are reported for the synthesis of α-tosyloxy ketones, using enol esters and chiral iodine(III) reagents. The reaction can be performed under both stoichiometric and catalytic conditions. These results suggest widely different reaction mechanisms for the reaction of ketones versus enol esters, supporting recent computational insights.
Catalytic enantioselective α-tosyloxylation of ketones using iodoaryloxazoline catalysts: Insights on the stereoinduction process
Guilbault, Audrey-Anne,Basdevant, Benoit,Wanie, Vincent,Legault, Claude Y.
, p. 11283 - 11295 (2013/02/23)
A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated α-tosyloxylation of ketone derivatives. The α-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.
Catalytic enantioselective α-oxysulfonylation of ketones mediated by iodoarenes
Altermann, Sabine M.,Richardson, Robert D.,Page, T. Keri,Schmidt, Ruth K.,Holland, Edward,Mohammed, Umal,Paradine, Shauna M.,French, Andrew N.,Richter, Christine,Bahar, A. Masih,Witulski, Bernhard,Wirth, Thomas
experimental part, p. 5315 - 5328 (2009/07/11)
The α-oxysulfonylation of ketones catalysed by enantio enriched iodoarenes using mCPBA as stoichiometric oxidant is reported to give useful synthetic intermediates in good yield and modest enantioselectivity. We believe this to be the first report of an enantioselective organocatalytic reaction involving hypervalent iodine reagents which should open up a new field for enantioselective organocatalysis of oxidation reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
