Enantioselective mercuriocyclization of gamma-hydroxy-cis-alkenes.
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.
Kang
Sung Ho
SH
Center for Molecular Design and Synthesis, Department of Chemistry, School of Molecular Science, Korea. shkang@kaist.ac.kr
Kim
Mihyong
M