74879-49-5Relevant academic research and scientific papers
Study of the Reactivity of [Hydroxy(tosyloxy)iodo]benzene Toward Enol Esters to Access α-Tosyloxy Ketones
Basdevant, Benoit,Legault, Claude Y.
, p. 6897 - 6902 (2015/10/06)
The reactivity of enol esters toward [hydroxy(tosyloxy)iodo]benzene (HTIB) was assessed. These substrates were found to be rapidly converted in high yields to their corresponding α-tosyloxy ketones. This transformation demonstrates that these substrates can act as ketone surrogates. The scope of the method was investigated and aromatic, aliphatic, and cyclic enol esters were found to be suitable substrates for the reaction. The relative reactivity of a model substrate toward HTIB and m-CPBA was investigated, and it was found that the reaction could be performed under catalytic conditions.
Enantioselective Iodine(III)-Mediated Synthesis of α-Tosyloxy Ketones: Breaking the Selectivity Barrier
Basdevant, Benoit,Legault, Claude Y.
supporting information, 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.
REACTION OF TRIALKYLBORANE WITH 1-ALKYNE AND LEAD(IV) ACETATE, A NEW REGIOSPECIFIC AND STEREOSPECIFIC ONE-POT SYNTHESIS OF ENOL ACETATES
Masuda, Yuzuru,Hoshi, Masayuki,Arase, Akira
, p. 413 - 416 (2007/10/02)
In the reaction of trialkylborane with 1-alkyne and lead(IV) acetate in hexane, one of the alkyl groups of trialkylborane migrated to the terminal carbon atom of the triple bond, giving regiospecifically an internal enol acetate and an internal alkyne as the main reaction products.The former compound had (Z)-configuration.
