Qizhi Ren
Corresponding author, tel: +86 21-54748943, fax: +86 21-54144589.
SPP full member in good standing.
School of Chemistry and Chemical Engeneering, Shanghai Jiaotong University, Shanghai 200240, China
Zongsheng Hou
School of Chemistry and Chemical Engeneering, Shanghai Jiaotong University, Shanghai 200240, China
Hong Zhang
School of Chemistry and Chemical Engeneering, Shanghai Jiaotong University, Shanghai 200240, China
Aiqin Wang
School of Chemistry and Chemical Engeneering, Shanghai Jiaotong University, Shanghai 200240, China
Shuangyan Liu
School of Chemistry and Chemical Engeneering, Shanghai Jiaotong University, Shanghai 200240, China

Received 11 November 2008
Accepted 23 April 2009

The chiral mono-faced binaphthyl strapped porphyrins were synthesized and ¹H NMR characterized. Asymmetric epoxidation of olefins such as styrene derivatives and trimethylsilyl ethylene with iodosobenzene as oxidant was achieved by using the iron complex as catalyst in the presence of a nitrogen ligand. Enantiomeric excess (ee) of 80% and yield of 88% were measured for the epoxidation of styrene in the presence of 4-phenyl pyridine. The coordination capability of nitrogen ligands to catalysts measured by UV-vis spectrophotometric titrations evidence that the unstrapped face of the mono-faced catalyst is blocked by the nitrogen ligand coordination to the iron ion of the catalyst.

mono-faced strapped porphyrin; asymmetric epoxidation; enantiomeric excess; nitrogen ligand; binding constant; coordination