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Catalytic, asymmetric vinylogous mukaiyama aldol reactions of pyrrole- and furan-based dienoxy silanes: how the diene heteroatom impacts stereocontrol

Curti, Claudio and Ranieri, Beatrice and Battistini, Lucia and Rassu, Gloria Maria Rita and Zambrano, Vincenzo and Pelosi, Giorgio and Casiraghi, Giovanni and Zanardi, Franca (2010) Catalytic, asymmetric vinylogous mukaiyama aldol reactions of pyrrole- and furan-based dienoxy silanes: how the diene heteroatom impacts stereocontrol. Advanced Synthesis & Catalysis, Vol. 352 (11-12), p. 2011-2022. eISSN 1615-4169. Article.

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DOI: 10.1002/adsc.201000189

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.

Item Type:Article
ID Code:5966
Status:Published
Refereed:Yes
Uncontrolled Keywords:Asymmetric catalysis, asymmetric synthesis, diastereoselectivity, enantioselectivity, heterocyclic dienoxy silanes, vinylogous aldol reaction
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Blackwell / Wiley
eISSN:1615-4169
Deposited On:19 Apr 2011 12:11

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