http://www.cnr.it/ontology/cnr/individuo/prodotto/ID169961
Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole- and Furan-Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol (Articolo in rivista)
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- Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole- and Furan-Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol (Articolo in rivista) (literal)
- Anno
- 2010-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1002/adsc.201000189 (literal)
- Alternative label
Curti, C.; Ranieri, B.; Battistini, L.; Rassu, G.; Zambrano,V.; Pelosi, G.; Casiraghi, G.; Zanardi, F. (2010)
Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole- and Furan-Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol
in Advanced synthesis & catalysis (Print); Wiley-VCH Verlag Gmbh, Weinheim (Germania)
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- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Curti, C.; Ranieri, B.; Battistini, L.; Rassu, G.; Zambrano,V.; Pelosi, G.; Casiraghi, G.; Zanardi, F. (literal)
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- http://onlinelibrary.wiley.com/doi/10.1002/adsc.201000189/abstract (literal)
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- Dipartimento Farmaceutico, Università degli Studi di Parma, Viale G. P. Usberti 27A, 43124 Parma, Italy;
Istituto di Chimica Biomolecolare del CNR, Traversa La Crucca 3, 07100 Li Punti, Sassari, Italy;
Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Università degli Studi di Parma, Viale G. P. Usberti 17A, 43124 Parma, Italy (literal)
- Titolo
- Catalytic, Asymmetric Vinylogous Mukaiyama Aldol Reactions of Pyrrole- and Furan-Based Dienoxy Silanes: How the Diene Heteroatom Impacts Stereocontrol (literal)
- 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 delta-hydroxylated gamma-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. (literal)
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