Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter

Autor: Francesca Franco, Sara Meninno, Jacob Overgaard, Sergio Rossi, Maurizio Benaglia, Alessandra Lattanzi
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Zdroj: Franco, F, Meninno, S, Overgaard, J, Rossi, S, Benaglia, M & Lattanzi, A 2022, ' Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter ', Organic Letters, vol. 24, no. 24, pp. 4371-4376 . https://doi.org/10.1021/acs.orglett.2c01589
DOI: 10.1021/acs.orglett.2c01589
Popis: A highly enantioselective one-pot synthesis of functionalized triflones, bearing a quaternary stereocenter, has been developed, exploiting the Michael reaction of α-(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.
Databáze: OpenAIRE