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  Extremely Active Organocatalysts Enable a Highly Enantioselective Addition of Allyltrimethylsilane to Aldehydes

Kaib, P. S. J., Schreyer, L., Lee, S., Properzi, R., & List, B. (2016). Extremely Active Organocatalysts Enable a Highly Enantioselective Addition of Allyltrimethylsilane to Aldehydes. Angewandte Chemie International Edition, 55(42), 13200-13203. doi:10.1002/anie.201607828.

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 Urheber:
Kaib, Philip S. J.1, Autor           
Schreyer, Lucas1, Autor           
Lee, Sunggi1, Autor           
Properzi, Roberta1, Autor           
List, Benjamin1, Autor           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Schlagwörter: allylic compounds; enantioselectivity; nucleophilic addition: organocatalysis; silanes
 Zusammenfassung: The enantioselective allylation of aldehydes to form homoallylic alcohols is one of the most frequently used carbon–carbon bond-forming reaction in chemical synthesis and, for several decades, has been a testing ground for new asymmetric methodology. However, a general and highly enantioselective catalytic addition of the inexpensive, nontoxic, air- and moisture-stable allyltrimethylsilane to aldehydes, the Hosomi–Sakurai[1] reaction, has remained elusive.[2, 3] Reported herein is the design and synthesis of a highly acidic imidodiphosphorimidate motif (IDPi), which enables this transformation, thus converting various aldehydes with aromatic and aliphatic groups at catalyst loadings ranging from 0.05 to 2.0 mol % with excellent enantioselectivities. Our rationally constructed catalysts feature a highly tunable active site, and selectively process small substrates, thus promising utility in various other challenging chemical reactions.

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Sprache(n): eng - English
 Datum: 2016-08-112016-10-062016-10-10
 Publikationsstatus: Erschienen
 Seiten: 4
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.1002/anie.201607828
 Art des Abschluß: -

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Titel: Angewandte Chemie International Edition
  Kurztitel : Angew. Chem., Int. Ed.
Genre der Quelle: Zeitschrift
 Urheber:
Affiliations:
Ort, Verlag, Ausgabe: Weinheim : Wiley-VCH
Seiten: - Band / Heft: 55 (42) Artikelnummer: - Start- / Endseite: 13200 - 13203 Identifikator: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851