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Asymmetric synthesis of (−)- and (+)-kainic acid using a planar chiral amide as a chiral building block

✍ Scribed by Katsuhiko Tomooka; Toshiyuki Akiyama; Phewluangdee Man; Masaki Suzuki

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
183 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

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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