Carbene-Catalyzed Activation of C-Si Bonds for Chemo- and Enantioselective Cross Brook-Benzoin Reaction.
Angew Chem Int Ed Engl
; 61(34): e202206961, 2022 08 22.
Article
em En
| MEDLINE
| ID: mdl-35696352
ABSTRACT
The first carbene-catalyzed asymmetric chemoselective cross silyl benzoin (Brook-Benzoin) reaction has been developed. Key steps of this reaction involve activation of the carbon-silicon bond of an acylsilane by a chiral N-heterocyclic carbene (NHC) catalyst to form a silyl acyl anion intermediate. These acyl anions then undergo an addition reaction with indole aldehydes in a highly chemo- and enantioselective manner to afford α-silyloxy ketones with excellent optical purities. The reaction mechanism of this cross Brook-Benzoin reaction was investigated through both experimental and computational methods. The chiral α-hydroxy ketone derivatives obtained by this approach show promising, agrochemically interesting activity against harmful plant bacteria.
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Base de dados:
MEDLINE
Assunto principal:
Benzoína
/
Metano
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article