Carbene-Catalyzed Activation of C-Si Bonds for Chemo- and Enantioselective Cross Brook-Benzoin Reaction.
Acylsilanes
Benzoin Condensation
Brook Rearrangement
Chemoselectivity
N-Heterocyclic Carbenes
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
22 08 2022
22 08 2022
Historique:
received:
12
05
2022
pubmed:
14
6
2022
medline:
19
8
2022
entrez:
13
6
2022
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 35696352
doi: 10.1002/anie.202206961
doi:
Substances chimiques
Ketones
0
carbene
2465-56-7
Benzoin
L7J6A1NE81
Methane
OP0UW79H66
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202206961Informations de copyright
© 2022 Wiley-VCH GmbH.
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Deposition Numbers 2008358 (for 4 g), 2165904 (for 6 d), 2067952 (for 14), and 2067953 (for 16) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
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