A highly enantioselective one-pot synthesis of functionalized triflones, bearing a quaternary stereocenter, has been developed, exploiting the Michael reaction of alpha-(trifluoromethylsulfonyl) aryl acetic acid esters with N-acryloyl-1H-pyrazole catalyzed by commercially available Takemoto's catalyst, followed by nucleophilic acyl substitution with alcohols. Preliminary investigations highlighted the attractive potential of the triflinate anion as the leaving group for stereocontrolled postfunctionalizations.
Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter / F. Franco, S. Meninno, J. Overgaard, S. Rossi, M. Benaglia, A. Lattanzi. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 24:24(2022), pp. 4371-4376. [10.1021/acs.orglett.2c01589]
Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter
S. Rossi;M. BenagliaPenultimo
;
2022
Abstract
A highly enantioselective one-pot synthesis of functionalized triflones, bearing a quaternary stereocenter, has been developed, exploiting the Michael reaction of alpha-(trifluoromethylsulfonyl) aryl acetic acid esters with N-acryloyl-1H-pyrazole catalyzed by commercially available Takemoto's catalyst, followed by nucleophilic acyl substitution with alcohols. Preliminary investigations highlighted the attractive potential of the triflinate anion as the leaving group for stereocontrolled postfunctionalizations.
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