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Synfacts 2008(10): 1114-1114  
DOI: 10.1055/s-2008-1078194
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Ti-Catalyzed Allylation of Aldehydes Promoted by Silica-Supported BINOL

Contributor(s): Yasuhiro Uozumi, Takao Osako
G. Liu*, Y. Gao, X. Lu, M. Liu, F. Zhang, H. Li*
Shanghai Normal University, P. R. of China
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Publikationsdatum:
22. September 2008 (online)

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Significance

A mesoporous silica-supported BINOL ligand (SBA-15/BINOL) was prepared by anchoring binaphthyl derivative 1 onto SBA-15 using Cl(CH2)3Si(OEt)3 (2) as a tethering agent, followed by TMS-capping and O-MOM cleavage. SBA-15/BINOL promoted the titanium-catalyzed alkylation of aromatic aldehydes with tetraallyltin under microwave conditions to give the corresponding homoallylic alcohols in 85.1-99% conversion with 92.5-99.9% selectivity.