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Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter.

ABSTRACT: 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.

SUBMITTER: Franco F 

PROVIDER: S-EPMC9490835 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter.

Franco Francesca F   Meninno Sara S   Overgaard Jacob J   Rossi Sergio S   Benaglia Maurizio M   Lattanzi Alessandra A  

Organic letters 20220610 24

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 <i>N</i>-acryloyl-1<i>H</i>-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 stereocontrolle  ...[more]

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