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Enantioselective Mercuriocyclization of γ-Hydroxy-cis-alkenes

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journal contribution
posted on 28.03.2003 by Sung Ho Kang, Mihyong Kim
Asymmetric mercuriocyclization of γ-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 K2CO3 worked beneficially.