Synthesis and stereochemical analysis of dynamic planar chiral oxa[7]orthocyclophene
Yukiho Hashimoto1, Yuuya Kawasaki1,2, Kazunobu Igawa3
1Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, Kasuga, Fukuoka 816-8580, Japan.
Abstract:
Planar chiral C6-substituted oxa[7]orthocyclophenes were designed and synthesized, and their stereochemical behavior was analyzed. The Kumada-Tamao coupling of the C6-iodo-substituted oxacyclophene enabled the efficient and divergent synthesis of C6-substituted derivatives. The stereochemical analysis of the oxacyclophenes revealed that the iodo- and methyl-substituted derivatives have reasonable stereochemical stability. The planar chirality of the methyl-substituted oxacyclophene was successfully transformed into central chirality by epoxidation without loss of enantiomeric purity.
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