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Modular chiral gold(i) phosphite complexes†Electronic supplementary information (ESI) available: Experimental results and NMR data. CCDC 933751 (L11(AuCl)), 933752 (L12(AuCl)a), 933753 (L9(AuCl)), 933754 (L10(AuCl)), 933756 (L8(AuCl)), 933757 (L12(AuCl)e). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3cy00250kClick here for additional data file.Click here for additional data file.

Delpont N, Escofet I, Pérez-Galán P, Spiegl D, Raducan M, Bour C, Sinisi R, Echavarren AM - Catal Sci Technol (2013)

Bottom Line: Chiral gold(i) phosphite complexes are readily prepared modularly from 3,3'-bis(triphenylsilyl)-1,1'-bi-2-naphthol.These chiral gold(i) phosphite complexes are very reactive precatalysts for the [4+2] cycloaddition of aryl-substituted 1,6-enynes with enantiomeric ratios ranging from 86 : 14 up to 94 : 6.

View Article: PubMed Central - PubMed

Affiliation: Institute of Chemical Research of Catalonia (ICIQ) , Av. Països Catalans 16 , 43007 Tarragona , Spain . Email: aechavarren@iciq.es.

ABSTRACT

Chiral gold(i) phosphite complexes are readily prepared modularly from 3,3'-bis(triphenylsilyl)-1,1'-bi-2-naphthol. These chiral gold(i) phosphite complexes are very reactive precatalysts for the [4+2] cycloaddition of aryl-substituted 1,6-enynes with enantiomeric ratios ranging from 86 : 14 up to 94 : 6.

No MeSH data available.


Synthesis of gold(i) phosphite complexes L12(AuCl)a–l from 3 and alcohols or phenols.
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sch3: Synthesis of gold(i) phosphite complexes L12(AuCl)a–l from 3 and alcohols or phenols.

Mentions: The preparation of a series of phosphite ligands(L12)a–n with different OR groups can be easily carried out using known methods31,32 from commercially available (R)-BINOL36 by known procedures via3,3′-bis(triphenylsilyl)-1,1′-bi-2-naphthol (3) (Scheme 3),37 which is also commercially available. Ligands(L12)a–n were routinely purified by chromatography on silica gel under an inert atmosphere and the corresponding gold(i) complexes L12(AuCl)a–n were prepared in quantitative yields by reaction with [AuCl(SMe2)].


Modular chiral gold(i) phosphite complexes†Electronic supplementary information (ESI) available: Experimental results and NMR data. CCDC 933751 (L11(AuCl)), 933752 (L12(AuCl)a), 933753 (L9(AuCl)), 933754 (L10(AuCl)), 933756 (L8(AuCl)), 933757 (L12(AuCl)e). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3cy00250kClick here for additional data file.Click here for additional data file.

Delpont N, Escofet I, Pérez-Galán P, Spiegl D, Raducan M, Bour C, Sinisi R, Echavarren AM - Catal Sci Technol (2013)

Synthesis of gold(i) phosphite complexes L12(AuCl)a–l from 3 and alcohols or phenols.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4317972&req=5

sch3: Synthesis of gold(i) phosphite complexes L12(AuCl)a–l from 3 and alcohols or phenols.
Mentions: The preparation of a series of phosphite ligands(L12)a–n with different OR groups can be easily carried out using known methods31,32 from commercially available (R)-BINOL36 by known procedures via3,3′-bis(triphenylsilyl)-1,1′-bi-2-naphthol (3) (Scheme 3),37 which is also commercially available. Ligands(L12)a–n were routinely purified by chromatography on silica gel under an inert atmosphere and the corresponding gold(i) complexes L12(AuCl)a–n were prepared in quantitative yields by reaction with [AuCl(SMe2)].

Bottom Line: Chiral gold(i) phosphite complexes are readily prepared modularly from 3,3'-bis(triphenylsilyl)-1,1'-bi-2-naphthol.These chiral gold(i) phosphite complexes are very reactive precatalysts for the [4+2] cycloaddition of aryl-substituted 1,6-enynes with enantiomeric ratios ranging from 86 : 14 up to 94 : 6.

View Article: PubMed Central - PubMed

Affiliation: Institute of Chemical Research of Catalonia (ICIQ) , Av. Països Catalans 16 , 43007 Tarragona , Spain . Email: aechavarren@iciq.es.

ABSTRACT

Chiral gold(i) phosphite complexes are readily prepared modularly from 3,3'-bis(triphenylsilyl)-1,1'-bi-2-naphthol. These chiral gold(i) phosphite complexes are very reactive precatalysts for the [4+2] cycloaddition of aryl-substituted 1,6-enynes with enantiomeric ratios ranging from 86 : 14 up to 94 : 6.

No MeSH data available.