Download PDF
Synfacts 2008(9): 0937-0937  
DOI: 10.1055/s-2008-1078680
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Stacked Paracyclophanes

Contributor(s): Timothy M. Swager, Eric L. Dane
M. Shibahara*, M. Watanabe, T. Iwanaga, T. Matsumoto, K. Ideta, T. Shinmyozu
Oita University, Kyushu University, Fukuoka and Okayama University of Science, Japan
Further Information

Publication History

Publication Date:
22 August 2008 (online)

    Permissions and Reprints

Significance

The authors report an improved synthetic strategy to form three- and four-layered [3.3]paracyclophanes (PCP). The use of the p-ethylbenzenesulfonyl group as opposed to the more commonly used p-tolylsulfonyl group provides better solubility of 2 and 5 in dichloromethane during the key coupling steps. Compound 4 was resolved into its enantiomers using chiral-HPLC, and meso compound 6 was separated from the diastereomers of 7 based on solubility.