Enantioselective mercuriocyclization of gamma-hydroxy-cis-alkenes.

J Am Chem Soc

Center for Molecular Design and Synthesis, Department of Chemistry, School of Molecular Science, Korea.

Published: April 2003

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/ja029777dDOI Listing

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