Asymmetric mercuriocyclization of gamma-hydroxy-(Z)-alkenes has been achieved using Hg(II) complexed with tartrate-derived 4-(2-naphthyl)bisoxazoline as chiral ligand to give rise to 2-monosubstituted tetrahydrofurans in 86-95% ee. Not only the linker connecting two oxazolines but also their 4-substituents were found crucial for high enantioselectivity. In addition, tuning the ketal protecting group of tartrate as well as adding MeOH and K(2)CO(3) worked beneficially.
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http://dx.doi.org/10.1021/ja029777d | DOI Listing |
Chem Commun (Camb)
June 2012
MIRC, Dept. of Chemistry, KAIST, Daejeon 305-701, Korea.
The enantioselective synthesis of (-)-dysiherbaine (1) has been established with efficiency via a unique synthetic strategy involving the desymmetrization of 2-substituted glycerol to install a quaternary chiral carbon, which induces further stereochemistry in the bicyclic perhydrofuropyran through mercuriocyclization and epoxidation.
View Article and Find Full Text PDFJ Am Chem Soc
April 2003
Center for Molecular Design and Synthesis, Department of Chemistry, School of Molecular Science, Korea.
Asymmetric mercuriocyclization of gamma-hydroxy-(Z)-alkenes has been achieved using Hg(II) complexed with tartrate-derived 4-(2-naphthyl)bisoxazoline as chiral ligand to give rise to 2-monosubstituted tetrahydrofurans in 86-95% ee. Not only the linker connecting two oxazolines but also their 4-substituents were found crucial for high enantioselectivity. In addition, tuning the ketal protecting group of tartrate as well as adding MeOH and K(2)CO(3) worked beneficially.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!