Denmark’s chiral bisphosphoramide/silicon tetrachloride system performs as an excellent Lewis base-Lewis acid catalyst for the vinylogous Mukaiyama aldol reaction of pyrrole- and furan-based dienoxy silanes with aromatic and heteroaromatic aldehydes. This asymmetric methodology provides a powerful synthetic entry to a variety of δ-hydroxylated γ-butenolide-type frameworks with high efficiency and valuable margins of regio-, diastereo-, and enantioselectivity. Notably, the nature of the heteroatom within the vinylogous dienoxy silane donor heavily impacts the diastereocontrol, with syn-configured aldol adducts emerging from pyrroles bearing electron-withdrawing N-protecting groups (Boc, Ts, and Cbz) and anti-configured adducts prevailing when furan- or N-alkyl/alkenylpyrrole donors are involved.

Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole- and Furan-Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol / Curti, Claudio; B., Ranieri; Battistini, Lucia; G., Rassu; V., Zambrano; Pelosi, Giorgio; Casiraghi, Giovanni; Zanardi, Franca. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 352:(2010), pp. 2011-2022. [10.1002/adsc.201000189]

Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole- and Furan-Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol

CURTI, Claudio;BATTISTINI, Lucia;PELOSI, Giorgio;CASIRAGHI, Giovanni;ZANARDI, Franca
2010-01-01

Abstract

Denmark’s chiral bisphosphoramide/silicon tetrachloride system performs as an excellent Lewis base-Lewis acid catalyst for the vinylogous Mukaiyama aldol reaction of pyrrole- and furan-based dienoxy silanes with aromatic and heteroaromatic aldehydes. This asymmetric methodology provides a powerful synthetic entry to a variety of δ-hydroxylated γ-butenolide-type frameworks with high efficiency and valuable margins of regio-, diastereo-, and enantioselectivity. Notably, the nature of the heteroatom within the vinylogous dienoxy silane donor heavily impacts the diastereocontrol, with syn-configured aldol adducts emerging from pyrroles bearing electron-withdrawing N-protecting groups (Boc, Ts, and Cbz) and anti-configured adducts prevailing when furan- or N-alkyl/alkenylpyrrole donors are involved.
2010
Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole- and Furan-Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol / Curti, Claudio; B., Ranieri; Battistini, Lucia; G., Rassu; V., Zambrano; Pelosi, Giorgio; Casiraghi, Giovanni; Zanardi, Franca. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 352:(2010), pp. 2011-2022. [10.1002/adsc.201000189]
File in questo prodotto:
File Dimensione Formato  
2010_Curti_ASC_abs.pdf

non disponibili

Tipologia: Abstract
Licenza: Creative commons
Dimensione 273.91 kB
Formato Adobe PDF
273.91 kB Adobe PDF   Visualizza/Apri   Richiedi una copia
2010_Curti_ASC_text.pdf

non disponibili

Tipologia: Documento in Post-print
Licenza: Creative commons
Dimensione 308.36 kB
Formato Adobe PDF
308.36 kB Adobe PDF   Visualizza/Apri   Richiedi una copia
n52_2010_ASC_SI.pdf

non disponibili

Tipologia: Altro materiale allegato
Licenza: Creative commons
Dimensione 3.7 MB
Formato Adobe PDF
3.7 MB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2302390
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 43
  • ???jsp.display-item.citation.isi??? 44
social impact