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Asymmetric deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides: formal synthesis of (–)-kainic acid

✍ Scribed by Clayden, Jonathan; Menet, Christel J.; Mansfield, Darren J.


Book ID
121827679
Publisher
Royal Society of Chemistry
Year
2001
Tongue
English
Weight
146 KB
Volume
1
Category
Article
ISSN
1359-7345

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Asymmetric synthesis of (−)- and (+)-kai
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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 followe