Bibliographic Details
| Title: |
Enantioselective Synthesis of the Excitatotry Amino Acid (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid. |
| Authors: |
Bradley, Daniel M., Mapitse, Renameditswe, Thomson, Nicholas M., Hayes, Christopher J. |
| Source: |
Journal of Organic Chemistry. 11/1/2002, Vol. 67 Issue 22, p7613. 5p. 5 Diagrams. |
| Subjects: |
Excitatory amino acids, Carbenes |
| Abstract: |
An enantioselective synthesis of the α,α-dialkyl-α-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent catalytic hydrogenation. Treatment of the ketone with 1.2 equiv of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the corresponding cyclopentene-containing CH-insertion product in 62-69% yield in high enantiomeric excess. Subsequent functional group manipulation allowed the synthesis of the amino acid (1S,3R)-ACPD to be completed. [ABSTRACT FROM AUTHOR] |
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| Database: |
Engineering Source |
