3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
Articolo
Data di Pubblicazione:
2020
Citazione:
3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions / S. Rossi, T. Benincori, L.M. Raimondi, M. Benaglia. - In: SYNLETT. - ISSN 0936-5214. - 31:6(2020 Apr 01), pp. 535-546. [10.1055/s-0039-1690777]
Abstract:
This account summarizes the development of new biheteroaromatic
chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine
oxides (BITIOPOs) have been successfully used as organocatalysts
to promote Lewis base catalyzed, Lewis acid mediated stereoselective
transformations. These highly electron-rich compounds, in combination
with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride),
generate hypervalent silicon species that act as chiral Lewis
acids in highly diastereo- and enantioselective organic reactions. Several
relevant examples related to these applications are discussed in detail.
1 Introduction
2 The BITIOPO Family
3 Enantioselective Opening of Epoxides
4 Enantioselective Allylation of Aldehydes
5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones
6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives
7 Conclusions
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
aldol reactions; chiral phosphine oxides; Lewis bases; organocatalysis; silicon hypercoordination; stereoselective reactions;
Elenco autori:
S. Rossi, T. Benincori, L.M. Raimondi, M. Benaglia
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