Palladium-Catalyzed Enantioselective Desymmetrization of Silacyclobutanes: Construction of Silacycles Possessing a Tetraorganosilicon Stereocenter

Palladium-Catalyzed Enantioselective Desymmetrization of Silacyclobutanes: Construction of Silacycles Possessing a Tetraorganosilicon Stereocenter

A palladium-catalyzed desymmetrization of alkyne-tethered silacyclobutanes to give silacycles possessing a tetraorganosilicon stereocenter has been developed, and high chemo- and enantioselectivities have been achieved by the use of a newly synthesized chiral phosphoramidite ligand.

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Veröffentlicht in:Journal of the American Chemical Society 2011-10, Vol.133 (41), p.16440-16443
Hauptverfasser: Shintani, Ryo, Moriya, Kohei, Hayashi, Tamio
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Crystallography, X-Ray
Models, Molecular
Molecular Structure
Organometallic Compounds - chemistry
Organosilicon Compounds - chemical synthesis
Organosilicon Compounds - chemistry
Palladium - chemistry
Silanes - chemical synthesis
Silanes - chemistry
Stereoisomerism
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Zusammenfassung:A palladium-catalyzed desymmetrization of alkyne-tethered silacyclobutanes to give silacycles possessing a tetraorganosilicon stereocenter has been developed, and high chemo- and enantioselectivities have been achieved by the use of a newly synthesized chiral phosphoramidite ligand.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja208621x