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Pure Appl. Chem., 2011, Vol. 83, No. 3, pp. 597-605

Published online 2011-01-21

Enantioselective construction of new chiral cyclic scaffolds using [2 + 2 + 2] cycloaddition

Takanori Shibata*, Toshifumi Uchiyama, Hiroyuki Hirashima and Kohei Endo

Department of Chemistry and Biochemistry, Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo, 169-8555, Japan

Abstract: Two types of enantioselective [2 + 2 + 2] cycloadditions of triynes using chiral rhodium catalysts are disclosed. The intramolecular reaction of ortho-aminophenol-tethered triynes provides chiral tripodal compounds. Consecutive inter- and intramolecular reactions of ortho-phenylene-tethered triynes provide chiral tetraphenylenes.