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
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.
Titolo: | 3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions |
Autori: | RAIMONDI, LAURA MARIA (Penultimo) BENAGLIA, MAURIZIO (Ultimo) (Corresponding) |
Parole Chiave: | aldol reactions; chiral phosphine oxides; Lewis bases; organocatalysis; silicon hypercoordination; stereoselective reactions; |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 1-apr-2020 |
Rivista: | |
Tipologia: | Article (author) |
Data ahead of print / Data di stampa: | 7-gen-2020 |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1055/s-0039-1690777 |
Appare nelle tipologie: | 01 - Articolo su periodico |
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