Novel Chiral Bis-Phosphoramides as Organocatalysts for Tetrachlorosilane-Mediated Reactions

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Sergio RossiMaurizio Benaglia

Abstract

The formation of novel chiral bidentate phosphoroamides structures able to promote Lewis base-catalyzed Lewis acid-mediated reactions was investigated. Two different classes of phosphoroamides were synthetized: the first class presents a phthalic acid/primary diamine moiety, designed with the aim to perform a self-assembly recognition process through hydrogen bonds; the second one is characterized by the presence of two phosphoroamides as side arms connected to a central pyridine unit, able to chelate SiCl₄ in a 2:1 adduct. These species were tested as organocatalysts in the stereoselective allylation of benzaldehyde and a few other aromatic aldehydes with allyl tributyltin in the presence of SiCl₄ with good results. NMR studies confirm that only pyridine-based phosphoroamides effectively coordinate tetrachlorosilane and may lead to the generation of a self-assembled entity that would act as a promoter of the reaction. Although further work is necessary to clarify and confirm the formation of the hypothesized adduct, the study lays the foundation for the design and the synthesis of chiral supramolecular organocatalysts.

References

Jun 21, 2001·Journal of the American Chemical Society·S E Denmark, T Wynn
Mar 18, 2005·Journal of the American Chemical Society·Scott E DenmarkMartin D Eastgate
Jun 25, 2005·Organic & Biomolecular Chemistry·Matthew J WilkinsonJoost N H Reek
Jul 13, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Albertus J Sandee, Joost N H Reek
Feb 20, 2007·Chemical Communications : Chem Comm·Albertus J SandeeJoost N H Reek
Feb 1, 2008·Angewandte Chemie·Scott E Denmark, Gregory L Beutner
Feb 7, 2008·Chemical Communications : Chem Comm·Andy Ch Laungani, Bernhard Breit
Jun 23, 2010·Organic & Biomolecular Chemistry·Maurizio Benaglia, Sergio Rossi
Feb 19, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Stefano CarboniUmberto Piarulli
Sep 6, 2014·Journal of the American Chemical Society·Scott E DenmarkHao Wang
Aug 23, 2016·Chemical Communications : Chem Comm·Mónica VaqueroAnton Vidal-Ferran

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Methods Mentioned

BETA
NMR
column chromatography

Software Mentioned

MetamorPhos

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