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The more gold - the more enantioselective: cyclohydroaminations of γ-allenyl sulfonamides with mono-, bis-, and trisphospholane gold(I) catalysts ; dedicated to Professor Peter Hofmann on the occasion of his 65th birthday

A series of chiral mono-, di-, and trinuclear gold(I) complexes have been prepared and used as precatalysts in the asymmetric cyclohydroamination of N-protected γ-allenyl sulfonamides. The stereodirecting ligands were mono-, di-, and tridentate 2,5-diphenylphospholanes, which possessed C1, C2, and C...

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Bibliographic Details
Main Authors: Rodríguez Broncano, Lara-Isabel (Author) , Roth, Torsten (Author) , Lloret Fillol, Julio (Author) , Wadepohl, Hubert (Author) , Gade, Lutz H. (Author)
Format: Article (Journal) Festschrift
Language:English
Published: 23 February 2012
In: Chemistry - a European journal
Year: 2012, Volume: 18, Issue: 12, Pages: 3721-3728
ISSN:1521-3765
DOI:10.1002/chem.201103140
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Festschrift
Online Access:Verlag, Volltext: http://dx.doi.org/10.1002/chem.201103140
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201103140
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Author Notes:Lara-Isabel Rodríguez, Torsten Roth, Julio Lloret Fillol, Hubert Wadepohl, and Lutz H. Gade
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Summary:A series of chiral mono-, di-, and trinuclear gold(I) complexes have been prepared and used as precatalysts in the asymmetric cyclohydroamination of N-protected γ-allenyl sulfonamides. The stereodirecting ligands were mono-, di-, and tridentate 2,5-diphenylphospholanes, which possessed C1, C2, and C3 symmetry, respectively, thereby rendering the catalytic sites in the di- and trinuclear complexes symmetry equivalent. The C3-symmetric trinuclear complex displayed the highest activity and enantioselectivity (up to 95 % ee), whilst its mono- and dinuclear counterparts exhibited considerably lower enantioselectivities and activities. A similar trend was observed in a series of mono-, di-, and trinuclear 2,5-dimethylphospholane gold(I) complexes. Aurophilic interactions were established from the solid-state structures of the trinuclear gold(I) complexes, thereby raising the question as to whether these secondary forces were responsible for the different catalytic behavior observed.
Item Description:Gesehen am 20.07.2018
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201103140

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