Asymmetric synthesis of (−)- and (+)-kainic acid using a planar chiral amide as a chiral building block |
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| Authors: | Katsuhiko Tomooka Toshiyuki Akiyama Masaki Suzuki |
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| Affiliation: | a Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga-shi, Fukuoka 816-8580, Japan
b Department of Applied Chemistry, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, Japan |
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| Abstract: | Both enantiomers of kainic acid have been synthesized from enantioenriched planar chiral cyclic amide 2a. The C3 and C4 stereocenters in the pyrrolidine ring were constructed by transannular Cope rearrangement of 2a, and the carboxyl group at the C2 position was introduced through lithiation followed by a carboxylation in the presence of an external chiral ligand. |
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